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Please login or sign up for a free trial to access the full content. Variation 1: Carboalumination of Alkenes and Alkynes

DOI: 10.1055/sos-SD-007-00207

Oishi, M.Science of Synthesis, (20047278.

The addition of organyl groups on an aluminum center to nonactivated CC multiple bonds possesses vast synthetic potential. In particular, dichlorobis(η5-cyclopentadienyl)zirconium(IV)-catalyzed methylalumination of alkynes has opened the ready entry of stereoselective methylated alkenyl groups to the syntheses of complex natural products. The reaction of organoaluminum compounds with alkenes, discovered by Ziegler and co-workers, is historically important.[‌165‌] This section summarizes noncatalyzed and metal-catalyzed carboalumination of alkenes and alkynes.

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Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeee[‌888‌,‌888‌]

Mee-8-eeeeeeeeeeee eeeeeeeee eeeeeeeee eee eeeeeeeeeeeeeeee ee 8,8-eeeeee, ee eee eeeeeeeeeeeeeee eeee eeeeeeeeeeeee, eeeeeee eeeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeeeee ee eeee eeeeeeeee eeee-eeeeeeee eeeee (Meeeee 88).[‌888‌‌888‌]

Meeeee 88 MeeeeeeeeeeeeeeeMeeeeeeeeee ee Meeeeeee[‌888‌,‌888‌]

Meeee eeee eeeeee eeeeeeee ee ee eeeeeeeeeee eeeee, eeeeeeeeeeeeeeeeee eeeeee ee eeeee eeeeeeeeeeeeeeeeeeeeee. Meee eeeeeeeee eeeeeee ee eeeeeeeeeeeeeeeeee eeeeeee eeeeeee eeeeeeee eeeeeeeeeee. 8,8-Meeeeeeeeeee-8-eeee, eeeeeeee ee eeeeeeeeeeeeeeee ee eeeeeee eeee eeeeee eeeeeeeeeeeeeee ee e eeeee eeeeee, eeeeeee eeeeeeeeeee ee eeee eeeeeeeeeeeeeeee eeee-eeeeeeee eeee eeeeeee (Meeeee 88).[‌888‌,‌888‌] Meeeeeeee, eee-eeeeeeee eeeee eee ee eeeeeeeeeee eeee eeee-8-ee-8-eee ee eee eeee eeeeee. Mee eeeeeeee eeeeeeeeeeeee eeeeeee ee eeeee e 8,8-eeeeeee eeeee, eeeeeeeee ee eee eeeeeeeee ee e eeee-eeeeee eeeeeee eeeeeeeeee eeeeeee.[‌888‌]

Meeeee 88 MeeeeeeeeeeeeeeeMeeeeeeeeeeeeeee Meeeeeee eee Mee-8-ee-8-eeee[‌888‌]

Meeeeeeeeeeeeeee ee eeeeeeeee, eeeee eeee eeeeee, eeeeeeee eeeeeeeeeee eee-eeeeeeee eeeeeeee ee eeee eeeeee.[‌888‌] Mee eeeeeeeeeeee eeeeee ee eeeeeeee. Mee eeeeeee, eeeeeeee eeeeeee, ee eeeeeeee ee eeeeeeeeeeeeeeee eeeeeeeeeeee, eeee ee eeeeeeeeeeeeeee eeeeeeeee eee eeeeeeeeeeeee, eee eeeeeeee eeee eeeeeeee eeeeeee eeeeeee eeeeeeeee, eeeeee eee eeeeeeeeeeeeeeeee. Meeeeeeee ee eeeeeeeeeeeeeee eeee ee ee8-eeeeeeeeee MeM eeee eee eeee eeeeeee eee eeeeeeeeeeeeeeee eeeeee eeee eeeeeeeee ee eeeeeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeeeeee ee e Meeeee Meeeee Meeeee α ee Meeeeeee ee Meeeeeeeeeeeeeee[‌888‌]

M eeeeeeeeee eeeeee ee eeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeee ee ee eeeeeeeee eeeeeee eee eeeeeeeeeeeee eeeeeeeeeeeeeeee ee eeeeeeeeeeee (Meeeee 88).[‌888‌] Meee eeeeeeeee eeeeeee eeeeeeeeee eeeeeeeee ee M,M- eee M,M-8-eeee-8,8-eeeeee.

Meeeee 88 Meeeeeeeeeeeeeee-Meeeeeee Meeeeeeeeeeeeeee ee Meeeeeeeeeee[‌888‌]

Meeeeee eee ee-eeeeeee eeeeeeee eee eeeeee- eee eeeeeeeeeeeeee eeeeeeeee ee eeeeeeeeeeeeee eeeeeee eee eeeeeeeeeeeeeeee ee eeeeeee ee eeeeeeeeeeeeeeeee eeeeeeeee eee ee­eeeeee­eee(η8-eeeeeeeeeeeeeeee)eeeeeeeee(MM).[‌888‌,‌888‌] Mee eee-eeeeeeeee eeeeee ee eee eeeeeeeeeee ee eee eeeee eeeeeeeeeeeee eeeeeeee ee eeeeeeee eeeeeee eeee eeeeee eeeeeeeeeeeeeee[‌888‌] ee eeeeeeeeeeeeee[‌888‌] eeeeeeeee. Meeeee, eee eeeeeeee eeeeeeee eeeeeeeeeeeee ee eeeeeee eee-eeeeeeeeeeeeeeee eeeeeeee eeeee eeee eeeeeeeeee. Mee eeeeee eee eeeeeeeeeeeeeee eee eeeeeeeeeeeee eeeeeeeee ee eeeeeeeeeeee eee eeeeeeeeeee ee eee eeeeeeee, ee eeeeeeeee ee Meeeee 88. Mee eeeeeeeeeeeee eeeeee eeeeeee ee eeeeeeeeeeeeeeeee eee eeeeeeeee ee ee eeeeeeeee(η8-eeeeeeeeeeeeeeee)eeeeeeeeeeeeeee(MM) ee e eeeeeee eeeeeeeee, eeeee ee MMM eeeeeee, eee e eeeee MeMe eeeeeeee eeeeeee eeeeeeee eee eeeeeeeee eee eeee eeeeeeee.

Meeeee 88 Meeee- eee Meeeeeeeeeeeeee Meeeeeeeeeeeeeee ee Meeeeee[‌888‌]

Meeeeeee eeeeeee eeee eee eeeeeeeeee eee eeee eeee eeeeeeee eeeeee ee eeeeeeee eeeeeeeeeeee. M eeeeeeee eeeeee eeee ee eee-8-eee eeeeeeeee eeeeeeeeeeeeeeee eeee eeeeeeeeeeeeeeeee ee eeee ee eeee eeeeeeeeeeeeeeeee. Meeeeee, eeee eee eeeee eee eeeeeeeeeeeeeeee ee eee eeeeeeeeeeeeeeeee eeeeeee eeee eeeee eeee eeeee ee eee eeeeeeeeeeeee eeeeeeee eeee eeeeeeeeeeeeeeeee, eee eeeeeeeee ee eee-8-eee ee 88% eeeee eeeeeeeee eeee eee eeeeeeee eeeeeeeeee eeeeeeee eeee β-eeeeeeeeeee ee eeeeeeeeeeeeeee eee eeeeeeeeeeeeeeee.[‌888‌] Meeeeeee eeeeeeeeeee eeeeeeee eee eeeeeeeeeeeeeeee ee eeeeeeee eee eeeeeeee eeeeeee eeee eeeeeeeeeeeeeeeee eeeeeeeee eeeeee eeeee, eeeeee, ee eeeeeeee eeeeee eeee eeeeeeee eeee eeeeeeee eeeeeeeeeee, eeeeeeee eee eeeeeee, eeeeeeeeeeeee ee eeeeeeeeeeeee, eee eee eeeeeeeee eeeeeeee.[‌888‌] Mee eeeeeee, eeeeeeee ee eeeee eeeeeee eeee eeeeee eeeeeeeeeeeeeeee eee eeeeeeeee eeeeeee ee eeeeeeeeeee(η8-eeeeeeeeeeeeeeee)eeeeeee­ee(MM) ee eeeeeee eeeeeeeee eeeeeeeeeeeeeeeeeee eeeeeeeeeeeee, eeeeeee ee eee eeeeeeeee ee eeeeeeeeeeeeeeee eeeee eeeeeeeee eeee eeeeeeeee eeeee (Meeeee 88). Meeeee eeee eeeeee eeeeeee eeeeeee eeeeeee eeeeeeeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeee ee ee Meeeeeeeeeeeeeeeeee Meeeeeeeeeee[‌888‌]

Meeeee eeeeeeeeeeeeee eeeeeeeeeeeeeeee ee eee-8-eeee eee eeeeeeee ee eeeeeeeee eee eeeeeeeeeee eeeeeeee eeee 8,88,88,88-eeeeeeeeeeeeeeeeeeee (MMM) eeeeeeeee eeeeeeeee, e.e. ee eee eeeeeeeee ee eeeeeee 88 eee 88 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeee Meeeeeeeeeeeeeee ee Meeeeeeeeeeeeeee[‌888‌]

Meeeeeee, eeeee- eee eeeeeeeeeeeeee eeeeeeeee, ee eeee ee eeeee eeeeeeeeeeeeeeeee eeeeeeeee eeee eeeeee eeeee eeeeee, eeee eeee eee eeeeeeeeeeeeeeee ee eeeeeeee eeeeeee ee eee eeeeeeee ee eeeeeeeeeee(η8-eeeeeeeeeeeeeeee)eeeeeeeee(MM) eee eeee eeeeeeee ee eeeeeeeeeeee eeee eeee eeeeee eee eeee eee eeeeeeeeeeeee, e.e. eee eeeeee 88 eee 88 eee eeeeee-eeeeeeeeeee eeeeeee 88 eee 88 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeee ee Mee-8-eeee eeee Meeee- eee Meeeeeeeeeeeee Meeeeeeee[‌888‌]

Me e eeeeee, eeee eeeeeeeeeeeeeeeee, eee eeeeee eeeeeeeeeeeeeeee eee eeeee ee eeeeeee eee eeee-eeeeeeee σ-eeee eeeeeeeeee, eeeeeee ee α-eeeeeeeeee eeeeeeee. Meeeeeeeeeeee, eeeeeeee ee 8.8 eeeeeeeeeee ee eeeee ee eee eeeeeeee eeeeeeeeeeeeeeee eeeeeeee eeeeee eeeeeeeeeeee eeeeeeee eee eeeeeeee eeee.[‌888‌] M eeeeeeeeeeeeeeeee eeeeee eee-eeeeeee eeeeeeeee eee eeeeeeee eeeeeee eee eeeeeee ee ee eee eeeeeeeeeeeee eeeeee eeeeeee eeee eeeeee eeeeee eeeeeeeeeeeeeee ee eeeeeee ee eee eeeeeeeeeeee eeee ee eee eeeeeeee ee eeeeeee eeeeeee ee eeeeeeeee eeeeeeeee.

M eeeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeeeeee(η8-eeeeeeeeeeeeeeee)eeeeeeee(MM) eeeeee eee eeee eeeeeee ee Meeeeee eee eeeeeee ee ee eeee eeeeeeee eeeeee eeeeeeee eeeeeee eeee eee eeeeeeeee-eeeee eeeeeeeeeeeeeeee.[‌888‌,‌888‌] Meeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeee eee eeeeeeeee ee 8,8-eeeeeeeeeeeeee ee 8888°M ee eeeeee eeeeeeeeeee M-eeeeeeeeee ee e eeeee ee 88% eeeee eeeee eeeeeeee eeee eeeeee. Mee-8-eee eeee ee eeeeeeeeee eeeeee ee 88% eeeee eeeeeee eeeeeeeeeeeeeeeee (Meeeee 88). Me eee eeeee eeee, eeeeeeeeeeeeeeeee eee eeeeeeee eeee eeeee e 8:8 eeeee ee eeeeeeeeeeeeeeeee eee eeeeeeeeeee(η8-eeeeeeeeeeeeeeee)eeeeeeee(MM), eeeeeee ee eee Meeee eeeeeee ee eee eeeeeeee ee e eeee. Mee eeeeee ee eeeeeeeee eee eeeeeeeeeeeeeee ee eeeeeee 8-eeeeeeeee eeeeeee, eeeeeeeee eeeeeeeeeee, -eeeee, -eeeeeeee, eee -eeeeeee eeeeeeeee (Meeeee 88).

Meeeee 88 Meeeeeee-Meeeeeee Meeeeeee Meeeee Meeeeeeeeeeeeee[‌888‌]

Meeeee 88 Meeeeeeeeeeeeee ee Meeee-Meeeeeeeeee Meeeeee[‌888‌]

Meeeeeeeeeeeee eeeeeeeeeeeeeeee eee eeee eeee eeeeeeee.[‌888‌] Meee, eeeeeeeeeeeeee eeeeeeeeeeeeeee ee eee eeeee eeeeee ee eeeee-eeeeeeee eeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeeee eee eeeeeeeee eeeeeeeeeee(η8-eeeeeeeeeeeeeeee)eeeeeeeee(MM) ee eeeeeeeeeeeeeee eeeeeeee ee eeeeee eeeeeeeeeeeeeee ee eeeeeee eeeee eeeeeeeeeeeee eee eeeeeeeeeeee eeeeeeeeee e eeeeeeeeeeeeee(eeeeeeeeeeeeeeeee)eeeeeeeee eeeee ee eeee eeeeee (Meeeee 88). Me eeeeeeeee eeeeeeeee ee eeee- eee eeeee-eeeeeeee eeee eeeeeeeee eee eee eeeeeeeeee.

Meeeee 88 Meeeeeeeeeeeeeeeeeeee ee Meeeeeeeeeee[‌888‌]

Me eeeeeee eeeeeeeeeeeeee eeeeeeeeeee eee eeeeeeee ee eeeeeeeee-eeeeeeeee eeeeeeeeeeeeeeeee ee 8-eeee-8-(eeeeeeeeeeeeee)eee-8-eeee.[‌888‌‌888‌] Me eeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeee-eeeeeeee σ-eeee eeeeeeeeeee, eeeeeeeeeeeeeeee eeeeeeeeeeeee eeeeeee π-eeee eeeeeeeeeee. Me eeeeeeee ee ee eeeeeeeeeee eee eeeeeeeeeeeeeeee, eee eeee eeee eeeeeeee ee 88 (M8=M; M8=Me) ee 88 (M8=Me; M8=M) eeeee eeeeeeeee eeeeeeeeee eeeeeeee ee eee eeeeeeeee ee 88 eeeeeeeeeeeee eeeeeeeee eeeeeeeeeeee 88 (Meeeee 88). Mee eeeeeee 88, eeeee eeeeee eeeeeeeeeeeeeeeee eeeeee ee eeee 88. Mee eeeeeeee eeee ee eeee eeeeeeeee eeee eeeeeee ee eeee eeee ee 8 8 >> 8 < 8.

Meeeee 88 Meeeeee-Meeeeeee Meeeeeeeeeeeeee[‌888‌‌888‌]

Mee eeeee- eee eeeeeeeeeeeeeee ee eeeeeeeeeeeeee eeeeee eeeeeeeeeeeeeeee eee eeee eeeeeeeeeeee. Meeeeeee-eeeeeeee eeeeeeeeeeeeeee ee eeeeeeee eeee eeeeeeeeeeeee eeeeeeeee eee eeeeeeee ee Meeeeee eee Meeeeeee'e eeeee.[‌888‌‌888‌] Meeeeeeeeeeee eeeeeeee eeee eee-eeeeeeeeeeeeeee eeeeeeee, ee eeeee eee eee MM eeee ee eeeeee ee eee M8 eeeeeeee. Me eee eeeee eeee, eeeeeeeee-eeeeeeeee eeeeeeeeeeeeeeee ee eeee eeeeeeeeee eeeee ee eeee eeeeeeeeeeee eeeeeeeeeee. Mee eeeeeeeee eeeeeeee eeeeee eeeeee eeeeee- eee eeeeeeeeeeeeee eeeeeeeeeeeeeeee ee eeeeeeeee eee eeeeeeeeeeeee eeeeeeeeeee eeeeeeeeee eeeeeee, eeee-eeeeeeeeeeeeeeeeeee, eeeeeeeeeeeeee, ee eeee eeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeeeeeeeeee Mee-8-eeee[‌888‌]

Meeeeeeeeee 88

M8 Meeee (%) Meeeeeeeeeeeeeee (%) Mee
(MM8)8MM 88 88 [‌888‌]
(MM8)8MMMMMM 88 88 [‌888‌]
(MM8)8M 88 >88 [‌888‌]
MM(MM)Me 88 >88 [‌888‌]
MM8MMe 88 >88 [‌888‌]

Meeeeee, eee-eeeeeeeeeeeeeeee eeeeeeee ee eeeeeeeee eeeeeeee, eeeeeeeeeeeeee- ee eeeeeee­eeeeeeee-eeeeeeeeee eeeeeeeee eeeeeeee, eee eeeee eeeeee eeeeeeeeee, eeeeeee eeeee eeeeeeeeeeeee ee eeeeeee, eeeeee eeee ee eee eeeeeeeeeeeee eeee-eeeeeeee (Meeeee 88). Mee eeeeeeeee-eeeeeeeeee eeeeeeeee eee eeeeeeeeeeeee eeee-eeeeeeeee eeeeee ee eeeeeee eee eeeeeeeee eeee eeee eeeeeeeeeeee.[‌888‌]

Meeeee 88 Meee Meeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeee 88

e M8 Meeeeeeeee eee Meeeeeeeeeeee Meeee (eeee/eee) Meeee (%) Mee
8 M eeeeee, 8e >88:8 88 [‌888‌]
8 MMM 88°M, 8e >88:8 88 [‌888‌]
8 MMM 88°M, 8.8e >88:8 88 [‌888‌]
8 MMM 88°M, 8.8e 88:88 88 [‌888‌]
8 MMM 88°M, 8.8e 88:88 88 [‌888‌]
8 MMM 88°M, 8e 88:88 88 [‌888‌]
8 MeMe8 88°M, 8.8e 88:8 88 [‌888‌]

Meee, eeeeeeeee-eeeeeeeee eeeeee eeeeeeeeeeeeeeee eeeeeeee eeeeee eeeeee- eee eeeeeeeeeeeeee eeeeeeeeeee ee eeeeeeeeeeeeeee eeeeeeeee. Mee eeeeeeeeee ee eeee eeeeeeeeeee eee eeee eeeeeeeeeeee ee eee eeeee eeeeee ee eeeeeeeeeeee eee eee eeeeeeeee ee eeeeeeeeeeee eeeeee eeeeeeeee, eeeeeeeee eeeeeeeeeeeeeeee,[‌888‌,‌888‌] MM-888,[‌888‌,‌888‌] 8888M,[‌888‌,‌888‌] eeeeeeeeeeeee,[‌888‌,‌888‌] β-eeeeeeee,[‌888‌] eeeeeeeeee,[‌888‌] eeeeeeeeeee,[‌888‌,‌888‌] eeeeeeeeeee M8,[‌888‌,‌888‌] eeeeeeeeee,[‌888‌] eeeeeeeeee,[‌888‌,‌888‌] eeeeeeeee,[‌888‌] eee eeeeeeeee M.[‌888‌]

Meeee 8 eeeee eeeeeeeee eeeeeeeeeeeeeeee ee eee-8-eeee ee eeeeee eeeeeeeeee eeee eee eeeeeeeeeee Meeeeee eeeeeeeeeeeeee eeeeee eee eee eeeeeeeee eeeee eeee eee ee eee eeeeeee: (8) eeeeee eeeeeeeee eeee e eeeeeeeeeee eeee eee (8) eeeeeeee ee eee eeeeeee eeee eee-eeeeee eeeee(MM), eeeeeee ee eeeeeeeeeeeeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeee Meeeeeeeeee ee Meeeee Meeeeeeeeeeeeeee

Mee eeeeeeee eeeeeee eeeeeeee e eeeeeeeeee eeee eeeeeeee eeeeeee ee 888eee%, eeeeeeee ee eeeeeeeee eeee eee eeeeee ee eeeeeee eee eeeeeeee ee eeee-eeeeeeee eeeeeee eeeeeeee. Meeeeeee ee eeeeeee eee eeeee eeeeee eeeeee eeeeee eeeeee, e.e. eeeeeeeeeeeeeeee eeeeeeeeeeeeeeee, eee eeee eeeeeee ee eeeeeee eeeeee.[‌88‌,‌888‌] Mee eeeeee eeeeeeeee eeeeeeee 88, eeeeeeeeee eeeeeeeee ee Meeee eee ee-eeeeeee,[‌888‌] eeeeeeeee eeeeeeeeeeeeeeeee ee eee-8-eeee eeee eeeeeeeeeeeeeeeee ee ee eeeeeeeeeeeeeeee eeeeee, eeeee eeeee eeeeeeeee eeeeee eeeeeeeee eeeeeeeee eee eeeeeeeeeee ee eeeee ee eeeeeeeeeeeeeeeeee (Meeeee 88).[‌888‌] Meee eeeeeeeeeeeeeeee ee eee-8-eeee eee eeeeeeeee ee eeeeee, eeeeeeeeeeeeeeeeeeee eeee eeeeee, eeeeeeeee ee eeee eeeeeeeeeeeee. Meeee eeeeeee eeeeeeeee, ee eee eeeee eeee eeeeeeeeee eeeeeeeeeeeeeeee eee ee eeeeeee eee ee eeeeeeeeeee eeeeeeee, ee eeeeeeeeee 8,8-eeeeeeeeeeeeee, eeee ee ee 88% ee (e.e., 88, Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeee Meeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 Meeee (%) ee (%) Mee
(MM8)8Me 88 88 [‌888‌]
eMe 88 88 [‌888‌]
Me 88 88 [‌888‌]
(MM8)8MM 88 88 [‌888‌]
(MM8)8MMe8 88 88 [‌888‌]

Meeeee 88 Meeeeeeeeeeeeeee Meeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 Meeeeeeeee Meeee (%) ee (%) Mee
Me Me 8°M, 88e 88 88 [‌888‌]
eMe Me 8°M, 88e 88 88 [‌888‌]
(MM8)8Me Me 8°M, 88e 88 88 [‌888‌]
(MM8)8Me Me 8°M, 88e 88 88 [‌888‌]
Me (MM8)8Me 8°M, 88e 88 88 [‌888‌]
Me Me 8°M, 88e 88 88 [‌888‌]
(MM8)8MMe8 Me 88°M, 88e 88 88 [‌888‌]

Meeeeeeeeeeee, eeeee eee eeeeeeeeeeeeeee (MMM) eeeeeee eee eeee ee eeeeeeeeeeeeeeee eee eee eeeee Meeee eeee eeeeeee eeeeeeeee ee eeeeeee ee eeeeeeeee eeeeee Meeeeee eeeeeeeeeeeeeeeeeeeeeeeeeeeee ee eeeeeee eeeeee eeeeee ee eee eeeeeeee ee 88, eeeeee eeeeeeeee eeeeee eeeeeeeeeeeeee eeeeeee (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeee MeeeeeeMeeeeeeeeeeeeeee ee Meeee Meee Meeeee: Meeeee ee Meeee[‌888‌]

Meeeeee eeeeeeeeeeeee eeeeee eee eeeeeeee ee e eeeeeeee eeeeee ee eeeeeeeeeeeeeeeeeee eeeeeeeeeee eee eeee(eeeeeeeeeeeeeeeee)eeeeee ee eeeeeee eeee-, eee-, eee eeeee-eeeeeeee eeeee eeee eeeeeeee ee eeee eeeeeeeeeeeeeeeeeeeeee (Meeeee 88).[‌888‌,‌888‌] Me eee eeeeeeee eeeeee, eee eeeeeeee eeee eeeeeee eeeeeee ee eee eeeeeeeee ee eee eeeeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeee eeeeee.

Meeeee 88 Meeeeeeeeeeeeeeeeeeee ee Meeeeeeeeeeee Meeeee[‌888‌,‌888‌]

Meeeeeeeeee 88

e M8 Meeee (%) Meeee (eee/eeeee) Mee
8 M 88 88:88 [‌888‌]
8 Me 88 8:888 [‌888‌]
8 Me 88 8:888 [‌888‌]
8 M 88 88:88 [‌888‌]
8 M 88 88:88 [‌888‌]

Meeeeeee-eeeee eeeeeeeeeee eeeeeeee eeeeeeeee 88 eee 88 eee eeee ee eeeeeeee (Meeeee 88).[‌888‌] Meeeeee, eeeeeeeee eeee eeeeeeeeeeeeeeeeeee eeeeeee ee eee eeeeeeeeeee ee eeee-eeeeeeee eeee-eeeeeeeeeee eeeeeeeee. Meeeeeeeeeeeeeee ee eeeeeeeeeeee ee eee eeeeeeee ee 88 eeee eee 8-eeeeee-8-eeeeeeeeeeeeee (88) eee eee eeeeeeeeeeeee eeeeeee 88.

Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeeee-Meeeeeeeeee Meeeeeee Meeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

(8M)-8-Meeeeeeeee-8-ee (88, M8=Me; M8=Me); Meeeeee Meeeeeeee:[‌888‌]

Me e eee, eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeeeee eee eee e Me eeeeeee eeee eeeeee 8,8-eeeeeeeeeeeeee (8eM), eeeeeeeee eeeeeeee 88 (88ee, 8.88eeee), eee Me8Me (8.88eM, 8eeee). Me eeee eeeeeee eee eeeee eee-8-eee (8.888eM, 8eeee) eeeee ee eeeee eeeeeeeeee. Meeee eeeeeeee eee eeeeeee ee 8°M eee 88e, M8 eee eeeeeee eeeeeee eee 88eee. Mee eeeeeeeee eeeeeee eee eeeeeee eeeeeee eeeee ee M8 eeeeeeeeee eee 8e, eeee eeeeeee eeee 88% ee MeMM, eeeeeeeee eeee Me8M, eeeeee eeee eeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee. Meeeee eeeeeeeeeeeeee (eeeeee eee, 8:8 Me8M/eeeeee) eeeeeeee eee eeeee eeeeeeee; eeeee: 88ee (88%); eee ee eee eeeeeeeeee eeee 8M MMM eeeeeee ee eee eeeeeeeeeeeee (+)- eee ()-MMMM eeeeee ee ee 88%; [α]M88 8.8 (e 8.8, MM8Me8).