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47.1.5.4.1 Method 1: Syntheses of Trisubstituted Alkenes via Zirconium-Catalyzed syn-Carboalumination of Alkynes

DOI: 10.1055/sos-SD-047-00410

Negishi, E.; Wang, G.Science of Synthesis, (201047978.

The discovery of the zirconium-catalyzed carboalumination of alkynes and its mechanism are discussed in the General Introduction (see Schemes 611).[‌9‌,‌16‌] As indicated by the results and the mechanistic findings, the current scope of the synthetically useful zirconium-catalyzed carboalumination with respect to the group to be added to an alkyne (R1CCH) as part of the organoaluminum (R2AlY2) is practically limited to those cases in which R2 is methyl, benzylic, or some allylic groups. Alkyl groups containing β-hydrogens exhibit a strong tendency to undergo β-agostic-interaction-induced cyclizing carbometalation leading to undesirable regioisomeric mixtures and dimetalated products. Efforts to suppress processes via cyclic intermediates and promote the desired noncyclizing process are called for. Despite this limitation with respect to R2, the reaction has been shown to be of very wide synthetic scope with respect to the R1 group of the terminal alkyne (R1CCH) as indicated in Schemes 1216 and other schemes presented further below. Practically all conceivable types of carbon groups including those containing various alkyl, allyl, benzyl, propargyl, aryl, alkenyl, and alkynyl groups as well as both proximally and remotely heteroatom-containing functional groups with halogens, oxygen, nitrogen, sulfur, phosphorus, silicon, and other heteroatoms have been satisfactorily employed. It is particularly noteworthy that, in most cases, high stereoselectivities (>99%), high regioselectivities (mostly 95%), and high product yields are observed. Some representative examples of the zirconium-catalyzed methylalumination (ZMA) reaction, by far the single most important case of alkyne carbometalation, applied to proximally heterosubstituted alkynes to give prop-1-enylaluminum derivatives such as 16 and 19, are shown in Schemes 1216.[‌38‌‌42‌] Halogenation of the alkenylaluminum compounds leads to alkenyl halides, e.g. 15, 17, 18, and20.

Meeeee 88 Mee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeee Meeeeeee ee 8-Meeeeeeeee-Meeeeeeeeee Mee-8-eeee[‌88‌]

Meeeee 88 Meeeeeeeeee ee eee M- ee M-Meeeee ee 8,8-Meeeee-8-eeeeeeeee-8-eee eeee Mee-8-ee-8-ee[‌88‌,‌88‌]

Meeeee 88 Mee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeee Meeeeeee ee e 8-Meeeeee-Meeeeeeeeee Meee-8-eee[‌88‌]

Meeeee 88 Mee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeee Meeeeeee ee e 8-Meeeeee- eee 8-Meeeeeee-Meeeeeeeeee Meee-8-eee[‌88‌]

Meeeee 88 Mee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeee Meeeeeee ee e 8-Meeee-Meeeeeeeeee Meee-8-eee[‌88‌]

Me eeeeeee eeeeeeeee ee Meeeeee 88.8.8.8.8.8, eeeeeeeeeeeeeee eeeeeeeee eeeeeeeee ee eee eeeeeeeee-eeeeeeeee eeeeeeeeeeeeeeeee (MMM) eeeeeeee ee eeeeeee eee ee eeeeeee eeeeeeeee eeee eeee eeeeeeeee ee eeeeeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeee, eeeeeeeeee, ee eeeeeeeee eeeeeeee ee eeee ee eee eeeeeeeeeeeee eeeee-, eeeeeee-, eee eeeeeeeee-eeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeeeeeee (eee eee eeeeee ee Meeeeee 88.8.8.8.8.8). Meeeeeeeeee, eee eee-, eee-, eee eeeee-eeeeee eeeeeeeeeeee eeeeeeeee eeeee ee eee eeeee ee Meeeeee 88.8.8.8.8.8 eeeeeee eeeeeeee eeeeeee eee MM eeee eeeeeeeee. Meeee eeeeeeeee eeeeeeeee eeeeeee ee eeeeeeeee eeee eeeeeeeee ee eeeeeeeeeeeee, eee eeee eee, ee eeee eeeee, eeeeeeeeeeee. Meee eeee ee eeeee eee eeeeeeeee ee eeeeee.

Meeeeeeee eeee eee ee eeeeeee ee eee eeeeeeeee-eeeeeeeee eeeee-eeeeeeee eeeeeeeee ee eeeeeeeeeeeee ee eeee 8 (eee Meeee 8, Meeeeee Meeeeeeeeeee) eeeeeeeeee eeeeee eeeeeeee eee/ee eeeeeee eeeeeee. M eeeeee ee 8888[‌88‌] eeeeeeeee eeee eeee 888 eeeeee eee eeeeeee eeeeeee eeeeeeee eee eeee eeeeeeeeeee ee eeeeee eee ee eee eeeeeeeee-eeeeeeeee eeeeeeeeeeeeeeeee eeeeeeee, eeee ee eeeee eee eeee eeeeeeee eee eeeeeeeee-eeeeeeeee eeeeeeeeeeee. Mee eeeee eeeeeeee eeee eee eee eeeeeeeee eeee, eee eeeeeee eee eeeeeeee ee eeee eeeeee.[‌88‌]

Meeeeeeee-eeeeeeeee eeeeeeeeeeeee eeee eeeeeeeeeeeee eee/ee eeeeeee eeeeeee ee eeee 8 eeeeeee ee eeeeeeeee-eeeeeeeee eeeeeeeeeeeeeeeee eee ee eeeeee ee eeee ee eee eeee eeeeeeeee eeeee. Me ee eee eeeeeeeee-eeeeeeeee eeeee-eeeeeeee eeeeeeee, eeeee eee eee eeeee ee eeeeeeeeee eeeeeeeeee: (8) eeeee eeeeeeeeeeeee eeeee (M); (8) eeeeeee eeeee (M); (8) eeeeeee (M); (8) eeeeeeeee eee eeeeeeeeeee; (8) eeeeeeee; eee (8) eeeee eeeeeeeeee, eeeeeeeee eeeeeeeeeee, eeee, eee ee ee (Meeeee 88).

Meeeee 88 Meeeeee Meeeeeeee-Meeeeeeee Meeeeeeeeeeee eeee β,β-Meeeeeeeeeeee Meeeeee Meeeeeee

Me eeeeeee eeeeee (M), eeeeee, eeeeeee, eee, ee eeee eeeee, eeeeeeee eeee eeeeee eeee eeee. Me eeee ee eee eeee 8 eeeeeee eeeeee eee eeeeeeeee ee eee eeeeeeeee-eeeeeeeee eeeeeeeeeeeeeeeee eeeeeeee, eeeeeeee eeeeee ee eeeeeeeeee eeeee ee eee eeeee, eee ee eee eeeeee ee ee eee ee eeeeeee eeeeeeeeeeee eeeeee. Me eeeeee, ee ee eeeeeeee ee eeeee eee ee eeee eeeeeeeeeee eeee eeeeeeee-ee-eeeeeeeee eeeeeeeeeeeeeee eee eeeeeeeeee,[‌88‌] eeeeeeee eeee eee eeeeee eeee eeeeeeee ee eee eeee. Me eeeeeeeee ee eeeee eeeeeeee, eeeeee eee eeeee eeee eeee eeee eeeee ee ee eeeeeeeeeeee, eeeeeeeeee eeee eeee eee eeee ee eeeeeeeeeee eeee eeeeeeeeeeeeee eee eeeeeeeeeeee. Me eeee eeeeee eeeeeeeee eeeee, eeeeeee, eeeeee eeeeeeee ee eeeeeeeee ee eeeeeeeeeeeeee eeeeeee ee eeee[‌88‌] ee eeeeee eeeee[‌88‌] ee, eeeeee eee, eeeeeeee eeeeeeeeee (Me ee M ee Me ee Me) eee ee eeeeeeeeee, eee eeeeee eeeeeee eeeeeeeeeeee eee eeeeeeeeeee eeee eeeeeeeee eeeeeeee. Mee eee ee eeeee eeee eeeee ee 8888[‌88‌] eeeeeeeeee eee eeeeeee eeeeeee eeeee eee eeee ee eeeeee eeeee eeeeeeeee.

Meeeeee (M) eeeeeeeee eee eeeeeee eeeeeeeee eeeeeeeee ee eeeeeee eeeeeeeeeeee. Meeeeeeeeee eeeeeeeee eeeeeee eeeee, ee eeeeeee eeee eee eeeeeeeeeeee eeeeeeeeee eeeeeeeeee ee eeeeeeeeeee eeeeeeeeeeeeeeeeee eee eee-8-eeeeeeeeeeeeee (MMM),[‌88‌] eee eeeeeeeee 8,8-eee(eeeeeeeeeeeeeeeee)eeeeeeeee,[‌88‌] 8,8-eee(eeeeeeeeeeeeeeeee)eeeeeee,[‌88‌] eee eee[8-(eeeeeeeeeeeeeeeee)eeeeee] eeeee (MMMeeee),[‌88‌] eee eeeeeee, eeee eee ee eeeeeeeeeeee eeee eeee eeeeee eeeeeeeee eeeeeeeee eee-eeee-eeeeeeeeeeeeee,[‌88‌,‌88‌] eeeeeeeeeeeeeeeeeeeeee,[‌88‌] eee eeee eeeeee. Meeee eee 8888e, eeeee eee-eeeeeeeee eeeeeee, eeee eeeeeee M-eeeeeeeeeeee eeeeeeee (eeeeeeeeeee ee eeeeeeeeeeee eeeeeeeee MMMMMM)[‌88‌] eeee eeeee ee eeeeeeeee eeeeeee eeee eeeeeeeeee. Me eeeeeee eeee eeee eeeeeeeee eee eeeeeeeee eeeeeee eeeeee eeeeeeeeeeee, ee eeeee ee eeeeeeeeeee ee eeeeeeee eeeee e eeeeeeeee ee eeeeeee eeeeeeeeeeee eee e eee eeeeeeee eeeeeeeeee eeeeeee, eeee ee eeeee eeeeeeeee eeeee eeeeeeeee eee M-eeeeeeeeeeee eeeeeee (MMMMMM), eee eeeee eeeeeeeeeee eeeeeeeeeee. Meeee eeeeeee eeee eeeeeeeee eeeee, eee eee eeee ee eeeeeee e eeeee ee eeee eeeeee. Me eeee eeeeeeeeeeee eeeeeeeeeeeee eeeeeeee, e eee ee eeee, eeeeeeeeeee eeeeeeeeeeee eeeeee eeeeeeeee eeeee eee eeeee ee eeeee; eeeeee eee eeee eee ee eeee eeeee eeeeeeeee eee eeeeeeee. Mee eee eeeeee, eeeeeeeeeeeeeee eee eeee eeeeee eeeeeeeeeeee eee ee eeeeeeeeee e eeee eeeeeeee eeeee. Me eeeeee, eee eee eeeee eeeeee eeee eeeee eeeeeeee, eeee ee eeeeeeeeeeeeeeeee, ee eeee eeeee eeee, eeee ee eeeeeee eeeee eee eeeeeee.

Me eeeeeeee ee M/M eeeeeeeeeeeee ee 8,8-eeeeeeeeeeeee eeeeeee, eeeee eee eeeeeee eeeeeeeee eeeeee ee eee M- eee M-eeeeeee eeeeee ee eeeeeeeeeeee, eee eeeeeeeeeeeeee eeeeeee eeeee eee eeeeee eeeee eeeeeeeee eeeee, ee eee eeeeeee, eee eee eeeeee, eeeeee- eee eeeeeeeeeeeeeee. Meee, ee eeee eeeee, eee ee eeee eeeeeeeee eeeeee eeeeeeeee eee eeeeeeee ee eeeee 88 eee ee eeeeeeee ee eeeeeeeeee eee eeee eeeeeeeeeeeeee eeeeeee. Me eeeeeee, eeeeeee, eeeee eee e eeeeee ee eeeeeeeee eeeeeeeeeee ee eee eeee ee eeeee eeeeeeeee eeeee ee eeeeeee eeeeeeee, eee eeeeeee eeeeeeeee eeee ee eeee ee eeeeeeee eee eeee eeeeeeeee eeeee ee e eeeee eeeeee. Me eeee eeeeeee, ee ee eeeee eeeeeeeee ee eeeeeeeeeee eee eeeee eee eeeeeeeeeeeee eeeeeeeeeeee eeeee ee eeeeeeeeeeeeee eeeeeee ee eeeeeeeeeeee, eeeeee eeee-ee-eeee eee eeee-ee-eeee eeeee (Meeeee 88). Mee eeee ee eee eeeeeeeeeeeeee eeeeee eeeeeee ee eee eeeeeee-eeeeeeeeeee eee ee eee M=M eeeeee, eeeeeee eee eeee ee eee eee eeeeeee e eeeeee eeeee eeeeeeeeeee.

Meeeee 88 Meee-ee-Meee eee Meee-ee-Meee Meeee ee Meeeeeeeeeee ee Meeeeeeeeeeeee Meeeeee

Mee eeeeeee, e eeeeee ee eeeeeeeee eeeeeeeee eeeeeeeeeeeeee eeeeeee, eeee ee eeeeeeeeeeee,[‌88‌‌88‌] eeeeeee α- eee/ee β-eeeeeeeeeee eeeeee eeeeeee. Mee ee eeeeeeeee eee eeeeeeeeee eeeeeeeeeeee ee e eee eeeeeeeeeeee 88 eee eee eeeeeeeee ee eeeeeeeeeeee, ee ee eeeeeeeee ee eee eee eeeeeee eeeeeeee eeeeee 88 ee 88. Mee eee eeeeeeeeeee ee eeeeeeeeeeeeeeee 88 eee eeeeeeeeee 88 eeee eeeeee 88, eeee-ee-eeee eee eeee-ee-eeee eeeeeeeeeeee, eeeeeeeeeeee, eeee eeee eeeeeeee, ee eeeeeeee ee Meeeeee 88 eee 88. Me eee eeee-ee-eeee eeeeeeeeeeee (Meeeee 88), e eeeeeeeeee eeeeee eeeeeeeeee ee eeeeeeeeeeeeeeee 88 eeee ee eeeeee eee eee eeeeeeeee-eeeeeeeee eeeeeeeeeeeeeeeee eeeeeeee ee eeeeeeee ee eeeeeee eeeeeee ee eeee 8 ee eeeeeeee ee e eeeeeeeeeee eeeeeeeeeeeeeeee eeeee eeeeeeee eeee eeeeeeeee ee eeeeeeeeeeeee ee <88% eeeee.[‌88‌] Me eee eeee-ee-eeee eeeeeeeeeeee ee eeeeee 88 (Meeeee 88), (M)-8-eeeeeeeeeee-8-ee ee eeeeeeeee eeee eeeeeee eeeeee 88, ee eeeeeeeee eee eeeeeeeeeeeeeeee ee eeeeee 88, eee eeeeeeeeee eeeeeeeee-eeeeeeeee eeeeeeeeeeee eeeeeeee.[‌88‌] Meee ee eee eeeeeeeeeeeee eeee eeeeeeeeee eeeee ee eee eee. Meeee eeeeeee eeeee ee eee eeee eee eeeeeeeee eee eeeeeeeeee eee eeeeeeeeeee eeeeee ee eeeeeee, eeeeeeeeee eeeeeeeeeeeee eeeeeeeee eeeeeeeeeeeeee eeeeeee.

Meeeee 88 Meee-ee-Meee Meeee ee ee Meeeeeeeeeee ee eee Meeeeeeee ee Meeeeeeeeeee[‌88‌]

Meeeee 88 Meee-ee-Meee Meeee ee ee Meeeeeeeeeee ee eee Meeeeeeee ee Meeeeeeeeeee[‌88‌]

Meee eeeeeeeeeeeeee eeeeeeee ee eeeeeeeee-eeeeeeeee eeeeeeeeeeeee eeee eeee 8 eeeeeee eeeeeeee eeeeeeeee ee eeeeeeeee-eeeeeeeee eeeeeeeeeeeeeeeee (MMM) eeeeeeeee ee eeeeeee eee eeeeeeeee eeee eeeeeeee ee eeeeeeeeeeee ee eeeeeee eeeeeee eeeeeeeee eeeeeeeee ee eee eeeee eeeeeeeee ee eee eeeee ee Meeeeee 88.8.8.8.8. Me eeeeee ee eeeeeeee eeee eeeeeeeeeee eeeeeeee, eee eeeeeee, ee eeee eeee ee eeeee ee eee eeeeeeee ee ee eeeeeeeeeeee eeee ee eeee eeeeeeeeeeee, eeeee eeeeeeeeeee eeeeeeee eeeeee ee eeee ee ee eeeeeeeee eeee ee eeeeeee eeeeeeeeeeee, eee eeee eeee eeeeeeeeeee ee eeeeeeeeee ee eee eeeee-eeeeeeee eeeee.

Meeeeeee, eeeeeeeeeee, eee eeeeeeeeeee eeeeeee: Me eeeeeeeeeeee ee eeeeeee eeeeeeeee 8,8-eeeeee ee eee eeeee eeeeeeeee ee Meeeeee ee Meeeeeeee, Mee. 88 [8,8-Meeeee (Meeeeee 88.888.8)], ee ee eee eeeeeeee ee eeee eeeeee. Meeeee 8888 eeee eeeeeeee ee eee eeeeeeeee[‌88‌] eee eeeeeeeeeeee[‌88‌] ee eeeeeeeeeeeeeeee, ee eeee ee eee eeeeeeeeeeeee ee ee eeeeeee eeeeee[‌88‌] ee eee eeeeeeeee ee e eeeeeeeee ee eeeeeeeeeee.

Meeeee 88 Meeeeeee Meeeeee eee M-β,β-Meeeeeeeeeeee Meeeeee Meeeeeee Meeeeee ee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeee[‌88‌]

Meeeee 88 Meeeeeeeeee Meeeeee eee M-β,β-Meeeeeeeeeeee Meeeeee Meeeeeee Meeeeee ee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeee[‌88‌]

Meeeee 88 Meeeeeeeeee ee Meeeeeeee-Meeeeeeee MeeeeeeMeeeeee Meeeeeee ee eee Meeeeeeee ee Meeeeeeeeee[‌88‌]

Meeeeeeee eee eeeeeeeeee eeeeeee: Me eeeeeeeee ee Meeeeee 88.8.8.8.8, eeeeeeeee-eeeeeeeee eeeeeeeeeeeeee eeeeeee eeeee eee eeeeeeeeeeeee eeeeeee, eee eeee eeeeeeee ee eee eeeeeeeee eeee. Me eeeeee eeee ee eeeeeeee eeee eee eeeeeeeee-eeeeeeeee eeeeeeeeeeee eeeeeeee eeeeee ee eeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeeeee eeeeeeee ee eeeee ee eeeee eeeeeeee eeeeeee eeeeeeeeeeeeee. Meeeeeeee, eee eee eeeeeeee eeeee ee Meeeeee 8888[‌88‌‌88‌] eeee ee eee eeeeeeee ee eeee α-eeeeeeeee (88),[‌88‌] eeeeee eeeeeee eeeeeeeeeeeee. Mee eeeeeee eeeeeeeee eeeeeeeeee eeee 88 (Meeeee 88),[‌88‌] eeeeeee eeeeeeeee eeee, eeeeee eee MeeeeMeeee eeeeeeeeee, eeeee eeeeeeee eeee eeeeeeeee eeeeeeee eeee eeeeee eeeeeeeee,[‌88‌] eee eeeeeeeee-eeeeeeeee eeeeeeeeee ee eeeeeeeeeeeee eeeeeeee eeee eeeeeeeee. Mee eeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeeee 88 eeee eeeee eeeeeeee 88 eeeee eeeeeeee M8 (88) ee 88% eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee Meeeeee eee M-β,β-Meeeeeeeeeeee Meeeeee Meeeeeee Meeeeee ee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeee ee e Meeeeeeee ee α-Meeeeeeee[‌88‌]

Meeeee 88 Meeeeeeee Meeeeee eee M-β,β-Meeeeeeeeeeee Meeeeee Meeeeeee Meeeeee ee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeee ee Mee-8-eee[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeeeeeeeeeeee ee eee Meeeeeeee-Meeeeeeee Meeeeeeeee ee ee Meeeeeeeeeee[‌88‌]

Meeeee 88 Meeeeeee ee ee M-β,β-Meeeeeeeeeeee Meeeeee Meeeeee Meeeeee ee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeee eeee ee Meeeeee Meeeee[‌88‌]

Meeeee 88 Meeeeeeee Meeeeee eee M-β,β-Meeeeeeeeeeee Meeeeee Meeeeeee Meeeeee ee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeee ee eee Meeeeeeee ee Meeeeeee M8 eee Meeeeeeeeee-8[‌88‌]

M eeeeee eeeeeee ee eeeeeeeee-eeeeeeeee eeeeeeeeeeeee eeeeeeee, eeeee eeeeeee eeeeee 88,[‌88‌] ee eeeee ee Meeeee 88, eeeee eeee eeeeeee eeeeeeee ee eeeeeeeeeeeee eeeeeeeee ee Meeeeee 88 eee 88.[‌88‌‌88‌]

Meeeee 88 M Meeeeeeeee Meeeee eee M-β,β-Meeeeeeeeeeee Meeeeee Meeeeeee Meeeeee ee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeee[‌88‌]

Meeeee 88 Meeeeeeeee Meeeeee eee M-β,β-Meeeeeeeeeeee Meeeeee Meeeeeee Meeeeee ee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeee 88

Meeeeeee Meee Meee (e) Meeee (%) Mee
Me(MMe8)8 eeeeee 88 88 [‌88‌]
MeMe8(MMe8)8 (8eee%), Me8M (88eee%), MeMe (88eee%) ee 8.88 88 [‌88‌]
MeMe8(MMe8)8 (8.8eee%), Me8M (8eee%), MeMe (8eee%) ee 8 88 [‌88‌]

Meeeeeeee eeeeeee: Meeeeeee eeeeeeeee eeeeeee eeeeeeeeee eee eeeeeee eeeeeeeeeee ee eeee 8 eee, ee eeeeeeeee, ee eeeeeeee ee eeeeeeeee-eeeeeeeee eeeeeeeeeeee eeeeeeee, e.e. eeeeeeee ee eeeeeeeeeeeee eeee eeeee eeeeeee, eeeeeeeee eee eeeeeeeee eeeee eeeeeeee eeeeeee eeeeeeeee-eeeeeeeee eeeeeeeeeeee eeeeeeee, eeeeeee eee eee eeeeeeeeeee ee eeeeeee eeeeeee ee eeee 8, eeeeee eeeeeee eee eeeeeeee. Mee eeeeeeeee-eeeeeeeee eeeeeeee ee eeeeeeeeee eeee M-8-eeee-8-eeeeeeeee-8-eeee ee eeeeeeeee eeee eeeeeeeeeeee, ee eeee ee eeeeeee eeeeeeeeee eee eeee (Meeeee 88).[‌88‌,‌88‌,‌88‌] Meee eeeeeeeee eee eeeeeeee eeeeeeeeee, eeeeeeeeeeeee eeee eeeeeee eeeeeeeeee ee eeeeeeee, ee ee ee eeeeeeee.

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeeeeee ee M-8-Meee-8-eeeeeeeee-8-eeee Meeeeeeeee ee Meeeee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeee Meeeeeeee eeee Meeeeeeeee[‌88‌,‌88‌,‌88‌]

Meeeeeeeeee 88

M8 M8M Meeee (%) Mee
Me MeMeMe 88 [‌88‌]
Me MeMeMe 88 [‌88‌]
Me M8M=MM(MM8)8MeMe 88 [‌88‌]
Me M8M=MM(MM8)8MeMe 88 [‌88‌]
Me e-MeMeMe 88e [‌88‌]
Me MMMMM(MM8)8MeMe 88 [‌88‌]
(MM8)8Me Me(MM8)8MeMe 88 [‌88‌]
(MM8)8Me MMMMM8MeMe 88 [‌88‌]

e Mee eeeeeee eeeeeeee e 88:88 eeeeeee ee eee e-Me eee eeeeeeeeee Me eeeeeeeeeee.

Meeeeeee eee eeeeee ee Meeeee 88, eeeeeee eeeeeeeeeeeee (e.e., 88) eeeee eeeeeeeeeeeeee eeee eeee 8 eee 8 eeeeeee eeeeeee (e.e., 88) ee eeee eee eeeeeeeeeeeee eeeeeeeeeeeeeee (e.e., 88), ee eeeeeeeee ee Meeeee 88.[‌88‌]

Meeeee 88 Meeeeeeee-Meeeeeeee MeeeeeeeMeeeeee Meeeeeee eeee β,β-Meeeeeeeeeeee Meeeeee Meeeeee[‌88‌]

Mee eeeeeeeee-eeeeeeeee eeeeeeee ee 8-eeee-8-eeeeeeeee-8-eeee eeee 8-(eeeeeeeeeeeeee)eee-8-eeeeeeee eeeeeee (eee Meeeee 88), ee eeeeee eee eeeeeeeee eee eeeeeeeee eeeeeeeee ee 8,8-eeeee-eeeeeeeeee eeeeeeeeee, eeee ee (8M,8M)- eee (8M,8M)-eeeeeeeee eee eeeeeeeeee (Meeeee 88).[‌88‌,‌88‌]

Meeeee 88 Meeeeeeee ee 8,8-Meeee-Meeeeeeeee Meeeeeeeee ee Meeeeeeee-Meeeeeeee Meeeeeee ee M-8-Meee-8-eeeeeeeee-8-eeee eeee 8-(Meeeeeeeeeeeee)eee-8-eeeeeeee Meeeeeeee[‌88‌,‌88‌]

Meee eeeeeeee, e eeee ee eeeeeeeee eee eeeeeeeee eeeeee eeee eeee eeeeeeeee eee eeeeeeeeee eee-8-ee-8-ee eeee (M)- eee (M)-8,8-eeeeee-8-eeeeeeeee-8-eeee (88) ee 88 eee 88% eeeeee, eeeeeeeeeeee, ee eee eeeee (Meeeeee 88 eee 88).[‌88‌‌88‌,‌88‌] Meee eeee (M)- eee (M)-8,8-eeeeee-8-eeeeeeeee-8-eeee eeeeeeeee ee eeeeeeeeeeee eeee eeeeeeeeeeee eeeeeeee eeeeeeee eeeeee, e eeee eeeee ee 8,8-eeeee-eeeeeeeeee eeeeeeeeeee ee eee eeeeeeeeeeeeee eeeeeeeeeee eee eee ee eeeeeeeeeee eee eeeeeeeeeee eeeeeeee, ee eeeeeeeee ee eee eeeeeeeee ee (8M,8M)- eee (8M,8M)-eeeeeeeee, (8M,8M,88M)-eeeeeeeeeeeeeee, eee eeeeeeee M88 eee eeeee eeeeeee 88, 88 [eeeee ee eeeeee ee 88% eeeeeee eeeee eeee (M)-88] eee 88. Meeeeeee M88 ee eeeeee ee 88% eeeee ee eeeee eeeee eeee (M)-88 ee eee eeeeeee eeeeee eeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee 8,8-Meeee-Meeeeeeeee Meeeeeeeee ee Meeeeeeee-Meeeeeeee Meeeeeee eeee (M)- eee (M)-8,8-Meeeee-8-eeeeeeeee-8-eeee[‌88‌]

Mee eeeeeeeee-eeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeeee-eeeeeeeee eeeeeeeeeeee eeeeeeee eeeeeeeeee eeeeeee eee eeee eeee eeeeeee ee eeeeeeeee eee eeeeeeeee eeeeeeeee ee e eeeeee ee eeeee eeeeeee eeeeeeee ee eeeeeeeee eeeeee.[‌88‌] Meeeeee eeeeeeeeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeee eeeeeee eeeeee ee eeeeeeeee-eeeeeeeee eeeeeeeeeeeeeeeee eeeeeeeee eee eeeee ee Meeeeee 8888.[‌88‌‌88‌]

Meeeee 88 Meeeeeeee ee Meeeeee eee Meeeeeeee-Meeeeeeee MeeeeMeeeeee Meeeeeee[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeeee M eee Meeeeeeee-Meeeeeeee MeeeeMeeeeee Meeeeeee[‌88‌]

Meeeee 88 Meeeeeeee ee eee 88-Meeeeeeeeeee Meeeeeee ee Meeeeeee ee Meeeeeeee-Meeeeeeee MeeeeMeeeeee Meeeeeee[‌88‌]

Meeeee 88 Meeeeeeee ee (+)-Meeeeeeeeeee M ee Meeeeeeee-Meeeeeeee MeeeeMeeeeee Meeeeeee[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeeeeee M eee Meeeeeeee-Meeeeeeee MeeeeMeeeeee Meeeeeee[‌88‌]

α,β-Meeeeeeeeee eeeeeeee eeeeeeeee eee eeeeeeee, eee β,γ-eeeeeeeeeee eeeeeeee eeeeeeeee: Meeeeeeeeeeee ee eeeee 8 ee 8 eee eee eeeeeeeeeeeee eeeeeee eeeeeee eeeeeee eeeeeeeee-eeeeeeeee eeeeeeeee (Meeeee 88),[‌88‌] eee eeeeeeeee (Meeeee 88),[‌88‌] ee eeee ee α-eeeeeeeeeeee ee eeeeeeee eeeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Me α,β-Meeeeeeeeee Meeeeeee Meeeeeee ee Meeeeeeee-Meeeeeeee Meeeeeeee ee ee Meeeeeeeeee[‌88‌]

Meeeee 88 M Mee-8-eeeeeeeeee ee Meeeeeeee-Meeeeeeee Meeeeeeee ee ee Meeeeee Meeeeee[‌88‌]

Meeeee 88 M β,γ-Meeeeeeeeee Meeeeeee Meeeeeee ee Meeeeeeee-Meeeeeeee α-Meeeeeeeeeee ee ee Meeeeeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

(M)-8-Meee-8-eeeeeeeee-8-ee-8-ee (88):[‌88‌]

MMMMMMM: Meee eeeeeeeeeeeeeeeee ee eeeeee eeeeeeeeee.

MMMMMMM: Meeeeeee eeeeeeeeeee eeee ee e eeeeee eeeeeeee ee eee eeeeeee eee eeeeee eeeeeeeee eeee eeeee.

Me e eeee ee Me(Me)8Me8 (8.88e, 8.8eeee) ee 8,8-eeeeeeeeeeeeee (88eM) eeee eeeeeeeeeeee eeeee eeee Me8Me (8.8eM, 88.8eeee) eee eee-8-ee-8-ee (8.88e, 8.8eeee) ee 8°M. Mee eeeeeeeee eeeeeee eee eeeeeee ee 88°M eee 8e eee eeeeeeeeee ee eee eeeeeeeeeeeeeeeee. Meeee MeMe8 eeeeee (8.88e, 88eeee) eee eeeee ee eee eeeee eeeeeee ee eee eeeeeee. Meeee eeeeeeee ee 88°M eee 8e, eee eeeeeeee eee eeeeeeee eeee e eeee ee M8 (8.88e, 88eeee) ee MMM (88eM) ee 88°M. Mee eeeeeeeee eeeeeee eee eeeeeee ee 88°M eee 88eee, eeeeee eeee eee eeeee, eeeeeeeee eeee Me8M, eeeeee eeee eeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee. Meeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8) eeeeeeee e eeeeee; eeeee: 8.88e (88%); 88% M-eeeeee.

(M)-8,8-Meeeee-8-eeeeeeeee-8-eee [(M)-88]:[‌88‌]

Meeeeeeee ee (M)-8-eeee-8-eeeeeeeee-8-ee-8-ee eeee Me8M, M8, eee eeeeeeeee ee MM8Me8 eeeeeeee eee eeeee eeeeeeee eeee 88% eeeeeeeeeeeeee eeeeee; eeeee: 88%.

α-Meeeeeeee (88):[‌88‌]

MMMMMMM: Meee eeeeeeeeeeeeeeeee ee eeeeee eeeeeeeeee.

Me e eeee ee Me8Me (8.88e, 8.88eM, 88eeee) eee Me(Me)8Me8 (8.88e, 8eeee) ee 8,8-eeeeeeeeeeeeee (88eM) eee eeeee ee ee eeeee M8 eee-8-ee-8-eee (8.88e, 88eeee) ee eeeeee. Meeee eee eeeeeee eee eeee eeeeeee ee ee eee 88e, eeeeeee eeeeeeee (8.88e, 88eeee), Me(MMe8)8 (8.88e, 8eeee), eee MMM (88eM) eeee eeeee ee 8°M. Mee eeeeeee eee eeeeeee ee ee eee 8e, eeeeeee eeee M8M (88eM), eee eeeeeeeee eeee eeeeeee. Mee eeeeeee eee eeeeee eeee ee MeMMM8 eee eeeee (MeMM8). Meeee eeeeeeeeee eee eeeeeeeeeeeee, eee eeeeeee eee eeeeeeeee; eeeee: 8.88e (88%).

Meeeeeee M8 (88):[‌88‌]

MMMMMMM: Meee eeeeeeeeeeeeeeeee ee eeeeee eeeeeeeeee.

Me e eeee ee Me8Me (8.88e, 8.8eeee) eee Me(Me)8Me8 (8.88e, 8.8eeee) ee 8,8-eeeeeeeeeeeeee (8eM) eee eeeee ee 88°M 8,88-eeeeeeeeeeeeee-8,8-eeee-8-eee (888ee, 8.8eeee). Mee eeeeeee eee eeeeeee ee 88°M eee 8e. Me eeee eeeeeee eeee eeeeeeeeeeee eeeee ee 8°M MMM (88eM), 8-(eeeeeeeeeeee)-8,8-eeeeeeeee-8-eeeeeeeeeee-8,8-eeeeeee (88; 888ee, 8eeee), eee Me(MMe8)8 (88ee, 8.88eeee). Mee eeeeeee eee eeeeeee ee 8°M eee 88eee eee eeeeeee eeee Me8M, eee eeeeeeee eee eeeeeeee eeee 8M MMe (eeeee eeeeeeee), eee eee eeeeeee eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8) eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeee eeeeeeeeeeeeee (eeeeee/MeMMe 88:8) eeeeeeee eee eeeee eeeeeeee ee e eeeeee eee; eeeee: 888ee (88%).

(8M,8M)-8-Meeeeeeee-8,8-eeeeeeeeeeee-8,8-eeee-8-ee (88):[‌88‌]

MMMMMMM: Meeeeeeee ee eeee-eeeeeeeeeeee eeeee eeeeeeeeeee eeee eeeee eee eee eeeeee ee eeeee eee.

Me (8M)-8-(eeee-eeeeeeeeeeeeeeeeeee)-8-eeee-8-eeeeeeeeeeee (8.8e, 8.8eeee) ee Me8M (88eM) eee eeeee 8.8M e-MeMe ee eeeeeee (8.8eM, 8.8eeee) ee 888°M. Meeee eeeeeeee ee 888°M eee 88eee, eee eeeeeee eee eeeeeeeeeee eeee e eeeee eeeeeeeeee MeMe8 (8.8e, 8.8eeee) ee MMM (88eM) ee 88°M. Meeee eeeeeeee eee 88eee ee 88°M, eee eeeeeee eee eeeeee eeeeee ee 88°M eeee 88eee. Me eeeeeee eeeee, (M)-8-(eeeeeeeeeeeee)-8,8-eeeeeeeeeeee-8-eee (88; 8.88e, 8.88eeee) eee eeeeeeeee ee MMM (88eM) eee eeeeeee eeeeeeeeeeeee eeee Me(MMe8)8 (88ee, 8.88eeee) eee eee eeeeeeeeee eeeeeee, eeeeeeee ee eeeeeeeee eeeee, ee 88°M. Meeee eeeeeeee eee 8e, eee eeeeeeee eee eeeeeeee eeee M8M, eee eee eeeeeee eee eeeeeeeee eeee Me8M, eeeeee eeee eeeee, eeeee, eeeeeeeeeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 8:8) ee eeee eee eeee-eeeeeeeeeeeeeeeeee-eeeeeeeee eeeee eeeeeeee ee e eeeeeeeee eee; eeeee: 8.88e (88%). Me eee eeeeeeeee eeeeeee (8.88e, 8.8eeee) ee MMM (8eM) eee eeeee 8M MMMM ee MMM (8.8eM, 8.8eeee) ee 8°M, eee eee eeeeeeeee eeeeeee eee eeeeeee ee 88°M eee 8e. Mee eeeeeeee eee eeeeeeee eeee M8M, eee eee eeeeeee eee eeeeee eeee eeeee, eeeee, eeeeeeeeeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 8:8) ee eeee eeeeeee 88 ee e eeeeeeeee eee; eeeee: 8.88e (88%).

References