Science of Synthesis

Lattanzi, A., Science of Synthesis: Stereoselective Synthesis, (2011) 3, 976.

In 1984, a modification of the Sharpless–Katsuki reagent for the asymmetric epoxidation of allylic alcohols was independently reported by the groups of Kagan and Modena.[‌24‌–‌26‌] The Sharpless–Katsuki asymmetric epoxidation of allylic alcohols with the titanium(IV) isopropoxide/diethyl tartrate/tert-butyl hydroperoxide system is described in Science of Synthesis, Vol. 37 [Ethers (Section 37.2.1.1.2)]. Under molar ratios optimized for the epoxidation, i.e. titanium(IV) isopropoxide/diethyl tartrate (1:2), the oxidation of prochiral sulfides is unselective. In contrast to the Sharpless–Katsuki oxidation of allylic alcohols, the stoichiometric oxidation of prochiral sulfides developed by Kagan requires a controlled amount of water in order to maintain a homogeneous system that results in high enantiocontrol. The reaction temperature and aging times for the generation of the catalytically active species are also found to be important parameters. Hence, a ratio of 1:2:1:1.1 titanium(IV) isopropoxide/diethyl tartrate/water/tert-butyl hydroperoxide is employed at −20 °C in dichloromethane to ensure an efficient and asymmetric oxidation (‌Scheme 4‌).[‌24‌,‌25‌]

‌Meeeee 8‌ Meeeeʼe Meeeeeee eee eee Meeeeeeeee Meeeeeeee ee Meeeeeee[‌88‌,‌88‌]

Mee eeeeeee eeeeeee ee eeeee ee eeeee eee eeeeeeeeee eeeeeeeee eee eeeeeeee eee eeee eeeeee eeeeeeeeee (88% ee), eeeeeeee eeeee eeeeeeeeeeeeeeeeee ee eeeeeeee eee eeeeeeeeee eeeee eee eeeeee eeeee ee eee eeeee eeeee ee eee eeeee eeee eeeeeee ee eeeeeeeee. Meee eeeeeeee eeeeeeeee eeeeeee eeeeeeeeee eeeeee ee eee eeeee eeeee eeeeeeeee eeeeee, eeeeeeeeeeee eeeee, eeeeee, eeeeeee, eee eeeeeee, eeeeee eeee eeee ee eeeeeeeeeeee eeeeeeeeeeeee eeeeeee eee eeeee ee eeeeeeeeee eeeeeeeee. Meeeeee eeeeeeeeee eee eeeeeeee eeee eeeee eeeeeeeeeeeeeeeeee (88–88% ee). Mee eeeeeee ee eeeeee eeeeeeeeeeeeee eee eee eeeeeee ee eee eeeeeeee ee eee eee ee eee eeeeeee. Mee eeeeeeee eeeeeeeeeeeee ee eeeeeeeee ee eeeeeeeeeee, eeeee eee (M)-eeeeeeeee ee eeeeeeee eeee (M,M)-eeeeeee eeeeeeee.

Meeee eeee eeeeeeeeeeee eee eeeeeeeee ee eeeeee eeeeee eeeeeeeeee eeeeeeeee.[‌88‌] Meeeeeeeee, eeeeeeeeeeee, eee eeeeeeeeee eee eeee eeeeee eeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeeee, eeeeeeeeeeee, eee eeeeeeeeee eee eeeeeee eeeeee eeeeee ee eeeeeeeeeeeeeeeeee, ee eeeeeeeeeee ee ‌Meeeee 8‌.

‌Meeeee 8‌ Meeeeeeeeeeeee Meeeeeeeee Meeeeeeee ee Meeeee Meeeeeee Meeee Meeeeʼe Meeeeeee[‌88‌]

‌Meeeeeeeeee 8‌

Mee eeeeeee eeeeeee eeeee eee Meeeeeʼe eeeeeeeee eeeeeeee ee 8:8:8 ee eeeeeeee(MM) eeeeeeeeeeee/eeeeeee eeeeeeee/eeee-eeeee eeeeeeeeeeeee ee eeeeeee ee 8,8-eeeeeeeeeeeeee ee −88 °M. ‌Meeeee 8‌ eeeeeeeeeee eeee eeeeeeee eee eee eeeeeeeee ee eeeeee 8-eeeee eeeeeeeee (‌8‌).[‌88‌] Meeeeee eeeeeee ee eeeee ee eeeeeeeeee eeeeeeeee eee eeeeeeee eeeee eeeee eeeeeeeeee ee eeeee eeeeeeee eeeee Meeeeʼe eeeeee. Meeeeeeeeeeee, eee eeeeeeee ee eeeeeeeee eeeeee eeeeeeee eeeeeee eeeeeeeeee, eeeeeeeeee eeee eeeee ee eeeeeeee eee eeeeeeeeee eeeeeeeee. Mee eeeeee ee eeeeeeee eeeeee ee eeeeeee ee eeeeeeeee eeeee, eeeee eeeee eeee eeee ee e eeeeeeeee eeeeeee eeeeeeeee ee eeee eeeeee eeeee Meeeeʼe eeeeeeeeee.

‌Meeeee 8‌ Meeeeeeee ee Meeeee 8-Meeee Meeeeee Meeee Meeeeeʼe Meeeeeee[‌88‌]

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

‌Meeeee 8‌ Meeeeeeeeeeeee Meeeeeeeee Meeeeeeee ee Meeeeeeee Meeeeeee eeee Meeeeʼe Meeeeeee Meeee Meeeee Meeeeeeeeeeee[‌88‌]

‌Meeeeeeeeee 8‌

Me eeeeeee eeeeeee, (M)-eeeee 8-eeeee eeeeeeeee ee eeeeeeee ee 88% eeeee eee eeee 88% eeeeeeeeeeee eeeeee. Meeeeeeeeeee, eeeee eeee eeeeeeee eeee eeeeee eeeee eeeeee eee eeee eeeeeeee eeee eeeeee eeeeeeeeee eeeeeeeee.

Mee eeeeeeeeee eeeeeeeee ee eeeeeee β-eeeeeee eeeeeeee eee eeee eeeeeee ee Meeeee.[‌88‌] M eeeeeeee eeeeee ee eeee eeeeeeee ee eee eeeeeeeee ee eeeeeee eee eeeeeee eeeee ee e eeeeeeeeee eeeeeeeeee eeeee eeeeeeeeee, eeeee eeeeeeeee eee eeeeeeeeee eeeeeee eee eee eeeeee eeeeee ee eee eeeeeeeee, ee eeeeeeeeeee ee eee eeeeeeeee ee {[8-(eeeeeeeeeeeeee)-8-eeeeeeeeeeee-8-ee]eee}eeeeeeeeeeeeeee (‌Meeeee 8‌). Meeeeeeee eeee eeee-eeeee eeeeeeeeeeeee eeeee eee eeee eeeeeeeeee eeeeeeee eee eeeeeeeee ee 88% eeeee, eeee ee 88:88 eeee/eee eeeee eee eeee 88% eeeeeeeeeeee eeeeee eee eee eeeee eeeeee.

‌Meeeee 8‌ Meeeeeeee ee {[8-(Meeeeeeeeeeeee)-8-eeeeeeeeeeee-8-ee]eee}eeeeeeeeeeeeeee eeeee Meeeeeʼe Meeeeeeeee[‌88‌]

MMM eee MM eeeeeee eeee eeee eeeeeee eee ee eeeeeeeee eee eeeeee ee eee eeeeeeeee eeeeeee eeeeeeee ee eee eeeeeee, eee eee eeeeeeeeeeeeee ee eeee eeeeeee ee eeeeeeeeeee eee ee eee eeeeeeee ee eee eeeeeeee eeeeeee ee eeeeeeee.[‌88‌] Meeee eeeeeeeee eee eeeeeeeeeeeeee eeeeeee ee eee eeeeeeeeee eeeeeeeee ee eeeeeeee ee eeeeeeeeee eee eeeeeeeeee eeeee eeeeeeeeeee ee ‌Meeeee 8‌.[‌88‌] M eeeeeeeeee eeeeeeeeeeeee eeeeeee ee eeeeee eeeee eee eeeeeeee eeee ee e eeeeeeeeee eeeeee. Mee eeeeeee eeeeeeeeee eeeee eee M—M eeee ee eee eeeeeeeeeee eeeeeeee eeeeeee ee eeeeeeeeeee eeee ee eeeeeeee ee eee eeeeeeeeeeeeeeee eeeeeeeeee eeeeeeee ee eee eeeeeee (MM) eee eeeeeeee (MM) eeeeeeeeeeee. Mee eeeeee eee eeeeeeeeee ee eeee ee MM eee MM, eee eeeeee eee eeeeeeeeeeeeeeeeee, eeeee ee eeeeeeeee eeeeeee eee eeee eeeeee eeeeeeeeee.

‌Meeeee 8‌ Meeeeeeeee Meeee Meeeeeee eee eee Meeeeeeee Meeee Meeeeʼe Meeeee[‌88‌]

Meeeeee eee eeeeeeeeeeee eee eeeeeeeee ee eee eeeeeeeee ee eee eeeee eeeeeeeeeeeee eeeee Meeeeeʼe eeeeeeeeee.[‌88‌] Me eeee eeee, eeeeee eeeeeeeeeeeee (8.8 eeeee), eeee e eeeeeeeeeeeeee eeeeee ee eee eeeeee eeeeeeee eeeeeee [eeeeeeee(MM) eeeeeeeeeeee/eeeeeee eeeeeeee 8:8], ee e eeeeeeee eeeeeee eeeeeeee ee eeee-eeeee eeeeeeeeeeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeeeeeeeee Meeeeeeeee Meeeeeeee ee Meeeeeeee Meeeeeee eeee Meeeeeʼe Meeeeeee Meeee Meeeee Meeeeeeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

e Meeeeeee eeee 88 e.

Meee eeeeee eeeeeeeeee eee eeeeeeeeeeeeeeee eeeeeeee ee eeee ee eeee eeeee eee eeeeeeeeeeeeeeeeee, eeee e eeeeeeeeeeee eeeeeee eeeeee eee eee eeeeeeeeeee ee eeeeee eeeee eeeeeeeee. Meeeeeeeeeee, eee eeeeeeeee eee eeeeeeeeeeeeee eeeeeeee ee eee eeeeeeee eeeeeee, eee eeeeeee eee eeeeeee eeeeee ee eeeeeeee eee eeeeeeeeeeeee eeeeee eeeeeee, eee eeeeeeee ee eeeee, eee eeee ee eeeeeeee ee eeeeeeee, eee eee eeeeee eeeeeeee eeee eee eeeeeee ee eeeeeeee eeeee eeeeee eee eeee eee eeeeeeeeeeee ee eee Meeee eee Meeeee eeeeeeeee.

Me eee eeeeee ee eeeeeee eeeeeeeeeeeeee ee eeeeeee e eeeeeeeee eeeeeee ee eee eeeeeeeee, Meeee eeeeeeee eeee eeeee eeeeeeeee eeeeeee (88 eee%) ee eee eeeeee eeeeeeee eeeeeee [eeeeeeee(MM) eeeeeeeeeeee/eeeeeee eeeeeeee/eeeee 8:8:8], eee eeeeeeee ee eeeeeeeee 8-Å eeeeeeeee eeeeee eeeeee eee eee eeeee eeeeeeeeee eee e eeeeeeeeee eeeeee ee eee eeeeeeeeeeeeeeeeee.[‌88‌,‌88‌] Meeeeeeee eeeeee eeeeee eeeeeeee eee eeeee eeeeee ee eeeee, eeeeeee ee eee eeeeeeee eeeeee, eeeee ee eeeeeeeeee eeeeeeeeeee eee eee eeeeeeeee ee eee eeeeeee eeeeeeee eeeeeeee eeeeeeeeeee eee eee eeeeee eeeeeeeeeeeeeeee eeeeeee. Me eee eeee eeeeeeee eeee eee eeeeeeeeeee ee eeeee ee eeeeee-8-ee eeeeeee eeeeeeeeee eeeeeee eeee eeeeeee ee eeeeeeee eeeeeeeeeeeeee eeeeeeeeee eeeee eeeeee eeeeeeeeeeeee. Meeeeeee, eeee ee eeee eeee, eee eeeeeee eeeeeeee ee eeeeeeeee eeeeee eee e eeeeeeee eeeeee. Meeee, e eeeee eeeeeeeee eeeeeeeee eee eee eeeeeeeee ee eeeeeeee eeee eeeeee eeeeeeeeeeeee (8 eeeee) eee eeee eeeeeeeeeee ee eeeeee eeeeeeeee eeeeee (8 ee eeeeeeeeee eeee eeeeeee ee eee eeeeeee) eee 88 eee% ee eee eeeeeee [eeeeeeee(MM) eeeeeeeeeeee/eeeeeee eeeeeeee/eeeeee-8-ee 8:8:8] ee −88 °M ee eeeeeeeeeeeeeee. Mee eeee eeeeee eeeeeeee ee eee eeee ee eeeeee 8-eeeee eeeeeeeee ee e 88% eeeee eee eeee 88% eeeeeeeeeeee eeeeee.[‌88‌]

Mee eeeeeeeee ee 8-eeeee-eeeeeeeeeee 8,8-eeeeeeeee eee 8,8-eeeeeeeeeee eee eeee eeee eeeeeeeeeeee eeee eee eeeeeeee(MM) eeeeeeeeeeee/eeeeeee eeeeeeee eeeeee.[‌88‌] Meeeee, eeeeeeeeeeeeeeee eeeeeeee eeeeeeeeeeeeee ee eeeeee eeeeeeeeeeeee eeeeeee eeeeee eeee eeeee eeeeeeeeeee eee eee eeeeeeeee eeeeeeeeeee eeeeeee. Meeeeeʼe eeeeeeeeee eeeeeeeee eeeeee eeeeee eeeeeee ee eee eeeeeeeee ee 8-eeeee-8,8-eeeeeeeeeee.[‌88‌,‌88‌] Mee eeeeeeeeeeeeee eeeeeee ee eeeeee eeeeeeeee eeeeeeeee eee eeeeeeee ee eeee eeeeeeeee- eee eeeeeeeeeeeeeeeeeeee eee eeeeeeee eee eee eeeeeeeeeeeeee (eeeee/eee 88:88 ee >88:88; 88–88% ee). Mee eeeeeeeee ee 8-eeee-8,8-eeeeeeeee, eeeee eee eeee eeeeeeeeee, eeeeeeeee eeeeeeee eeee eeee eeeeeeeeeeeee, ee eeeeeeeeeee ee ‌Meeeee 88‌.[‌88‌–‌88‌] Meeee eeeeeeeeeeeeee eeeeeee ee eee eeeeeeee(MM) eeeeeeeeeeee/eeeeeeee eeeeeee eeee eee Meeeee ee Meeee eeeeeeee, (8M,8M)-eeeeeeeeee eeeeeeeeee eee eeeeeeee ee eee eeeee eeeeeeee ee eeee eeeee eeee eeeeeeeeeeee eeeeeeeeeeeeeeeeeeee eee eee eeeee-eeeeee ‌8M‌ eee eeee eeee eeeeeeeeeeee eeeeee. Mee eeeeeeee ee eee eeeeeeeeee eeeeeeeeeeeeee, eeeee eee eeeee-8,8-eeeeeee ‌8‌ ee eeeeeeee ee eee eeeeeeeee ee 8-(8-eeeee-8,8-eeeeeee-8-ee)eeeee-8-eee eee eeee-eeeee 8,8-eeeeeeee-8-eeeeeeeeeee ee 8 eee 88% eeeee, eeeeeeeeeeee. Me eeee eeeee, eee eeeee-8,8-eeeeeee ee eeeeee eeeeeeeeeeeeeeee eeeeeeee ee eeeeeeee. Meee eeeeeeeee eeeeeeee e eeeeeeeeee eeeeee ee eeeeeee e eeeee-(8M,8M)-8,8-eeeeeeee 8,8-eeeeeee eeeee Meeeeeʼe eeeeeeee ee >88% eeeeeeeeeeee eeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeeee Meeeeeeeee Meeeeeeee ee 8-Meee-8,8-eeeeeeeee eeee Meeeeeee(MM)/(M,M)-Meeeeee Meeeeeee Meeeeee[‌88‌,‌88‌,‌88‌]

‌Meeeeeeeeee 88‌

e e.e. = eee eeeeeeeeee.

Mee eeeeee eeeeee eeeeeeeee ee 8,8-eeeeeeee eeeee Meeeeʼe eeeeeeeeee eeeeeee eeeee-(8M,8M)-8,8-eeeeeeee 8,8-eeeeeee eeee eeeeee eeeeeeeeeeee eeeeee (88% ee).

Meeeeeee ee eeee eee eeeeeeee/eeeeeeee eeeeee eeee eeeeeeeee eeee eee ee eee eeeeeeeeeeeeee ee eee eeeeeeee eeeee eeeeeee eeeeeeee; eeeee eeeeeee eeeee eee eeeeeeeeee ee eeeeeeeeeee eeeeeeee eeeeeeeee, eeee ee eeee eeeeeeeeee, eeee ee eeeeeeeee eeeeeeeee, eee eee eeee eeee eeeeeeee eee ee eeeeeee eeeeeeee, eeeeeeee, eee eeeeeeee.[‌88‌] Meee(eeeeeeee eeeeee) eeeeeeeeee eeeee (MeMMMMMM) eeeeeeee e eeeeeee eeeeeee eee e eeeee eeeeeee ee eeeeeeee eeeeee (e.e., ‌8‌), eeeee eee eeeeeee eeeeeeeee eee e eee-eee eeeeeeee eeeee (M,M)-eeeeeeee eeee, eeee(eeeeeeee eeeeee) eeeeeeeeee eeeee (MM 8888), eee eeeeeee eeeeeeee (‌Meeeee 88‌). Mee eeeeeeeee eeeee eeeeee eeeeeeeeeeeee eee eee eeeee eeeeeee ee eeeeeeeeeeeeeeeee eeeeeee (88 eee%) ee eeeeeeeeeeeeeee ee −88 °M, eeeeeeeee eee (M)-eeee eeeeee eeeeeeeeee ee eeee eeeee eee eeee eeee eeeeeeeeeeeeeeeeee. Mee eeeeeeee eeeeeee eee eeee eeeeeeee ee ee eeee eeeee eeee >88% eeeeeeee eeeeeee eeeeeeeeeeee eee eeeee ee eeeeeeeeee eeeeeeeee ee eee eeeeeeeee, eee eee eeeeeeee eee ee eeeeee eeeeeeeee ee eeeeee eeeeeeeeeeeee eee eeeeeeeeee.

‌Meeeee 88‌ Meeeeeeeeeeeeeee Meeeeeeee ee Meeeeeee Meeee e Meeeeee-Meeeeee-Meeeeeeee Meeeeeee Meeeee[‌88‌]

‌Meeeeeeeeee 88‌

Meeeeeee(MM)/eeeeeee eeeeeeee eeeeeeeee eeeeeeeee ee eeeeeeee eee eeeeee ee ee e eeeeeeee eeeeeeeeeeeeee eee eee eeeeeeeeeee ee eeeeee eeeeeeeeeeeeeee eeeeeeeeee eeee eeeeeeeee eeeeeeeeee eeeeeeee. Mee eeeeeee ee eee eeeeeeeeee eeeeeeeeee ee eeeeeeeeeeee ee MeeeeMeeeee [eeeeeeeeeeee, eee M-eeeeeeeeee ee eeeeeeeeee, ee eeeeeeeeee ee Meeeeee]. Meee eeeeeeeee ee e eeeeee ee e eeeeee eeeeee eeeee ee eeeeeee eeee eeeeeeeee eeeeeeeeee, eee ee eeeeeeeeeeee eeee ee ee eeee-eeeee eeeee.[‌88‌] M eeeeeeee eeeeeeeee eeeeeee ee Meeeeʼe eeeeeeee eee eeeeeee ee eeeeeee eeee eeeee. Meee eeeeeeeeee eee ee eee eeee eeeeeeeee eeeee-eeeee eeeeeeeeee eeeeeeeeee eeeeeeeee ee eeee ee eee eeeeeeeeeeeeee eeeeeeee (‌Meeeee 88‌).[‌88‌,‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeeeeee Meeeeeeee Me Meee Meeeeeeeeeee[‌88‌]

Mee eeeeeeee eeeeeeeee eeeeeeee eeeeeeee eeeeee eeeeeee eeeeeeeee, eeeeeeeeee eee ee eee eeeeeeeeee eeee ee eee eeeeeee eeeeeeeeeeee. Mee eee eeeeeeee, eeeeeee eeeee ee eee eeeeeeee, eeeeeeee eee eeeeeeeeeeee ee M,M-eeeeeeeeeeeeeeeeeeeee (Müeeeʼe eeee) ee eeeeeee eeeeeeeee eeeeeeeeeeeeeeeeee. Meeeee, eeeeeeeeeeee ee eeeeeeee ee 88% eeeee eee eeee 88% eeeeeeeeeeee eeeeee eeeee eeeeeeeeeeeeeeeee eeeeeeee ee eee eeeeeeee eeeeeeee (8–88 eee%).[‌88‌] Meeeeeee, e eeeeeee ee eeeeeee eeeeeeee eeee eee eeeeeeeee MM eeeee eee eeeeeeee eeee eeee eeeeeeeeeeeeeeeeee. M eeeeeeeeeee eeeeeeeee eee eee eeeeeeeee ee eeeeeeeeeee eee eeeeeeeeeeee eeeeeee eeeeeeee eeeee ee MM, MMM, eee MMM eeeeeeee eeeeeee eee eeee eeeeeeee. Meee eeeeeeeee eeeeeeee eeee eee eeee eeeeeeeee eeeeeeeeeee eeeeeeeee eeeeeeeeee eeeeeeeee ee eee eee-ee-eeeeee eeeeeeeee ee eeeeeeee eeeeeee eeeeeee eee MM ee eee eeeeeeeee eeee eee eee eeeeee eeeeeeee eeeeee ee eee eeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeee Meeee Meeeeeeee ee eee Meeeeeeee ee e Meeee Meeeee Meeeeeeee Meeeeee[‌88‌]

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

‌Meeeee 88‌ Meeeeee Meeeeeeeee ee Meeeee Meeeeeeeee[‌88‌,‌88‌]

‌Meeeeeeeeee 88‌

e e = ee[(8 – M)(8 – ee)]/ee[(8 – M)(8 – ee)];[‌88‌] e.e. = eee eeeeeeee.

Mee eeeeeeeeeeeeeeee eeeeeeeee/eeeeeee eeeeeeeeee ee eeee eeeeee eeeeeeee eee eeeeeee eeeeeeee, eeeee ee eeeeee ee eeeee eeeeeeeeeeeee ‌8‌ (8.8 eeeee) eeeee eeeeeeeeeeeeee eeeeeeeeee [eeeeeeee(MM) eeeeeeeeeeee/eeeeeee eeeeeeee 8:8] ee eeeeeeeeeeeeeee ee −88 °M, eeeeeeee eeeeeee eeeeeeeeee ee eeeeee eeeee (88–88%) eee eeee eeee ee eeeeeeeee eeeeeeeeeeeeeeeeee (88–88% ee).

Meeeeeeeeeee Meeeeeeee

(M)-Meeeee 8-Meeee Meeeeeeee (‌8‌); Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeee eeee ee Me(MeMe)8 (8.8 e, 8.8 eeee) eee (M,M)-MMM (8.8 e, 88 eeee) ee eeeee 8,8-eeeeeeeeeeeeee (88 eM) eeeeee ee −88 °M eeee eeeee eeeeeeeeeeee e-MeMMM (8.8 e, 88.8 eeee, ee eeeeeeee) eee eeeeee 8-eeeee eeeeeee (8.88 e, 8.8 eeee). Mee eeeeeee eee eeeeeee ee −88 °M eee 88 e, eee eeee eeeeee eeee 8% ee Me8MM8 (8 × 88 eM) eee eee. ee MeMe. Mee eeeeeee eeeee eee eeeee (MeMM8) eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MMMe8); eeeee: 8.88 e (88%); 88% ee [eeeeeeeeee eeeee eeeeeee eeeeeeeeeeee (ee 88–88 °M/8.8 Meee)].

(M)-Meeeee 8-Meeee Meeeeeeee (‌8‌, M8 = 8-Mee); Meeeeee Meeeeeeee:[‌88‌]

Me(MeMe)8 (8.88 e, 8 eeee) eee eeeee eeeeeee (88 e) ee e eeee ee (M,M)-MMM (8.88 e, 8 eeee) ee MM8Me8 (88 eM) eeeee M8 ee 88 °M. Meeee 8.8 eee, M8M (88 µM, 8 eeee) eee eeeee eeeeee eeeee e eeeeeeeeee eeeeeee eeee eeeeeeee eeeeeeee eee ee eeeeeeeeeeee ee 88 e eeeee eeee eeee. Mee eeeeeee eee eeeeeee eee 88 eee ee 88 °M, eeeeeeee ee eeeeeee ee e eeeeeee (−88 °M) eeeeeee eeeeeeee eee ee eeeeeeeeee 88 eee. Meeee eeeeeeee ee eeeeee 8-eeeee eeeeeee (888 ee, 8 eeee) eee eeeeeeeee (−88 °M) eeeeee eeeeeeeeeeeee (8 eeee) eee eeeeeeee ee eeeeeee ee eee eeeee ee eee eeeeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeee eeee e eeee ee MeMM8•8M8M (8 e, 88.8 eeee) eee eeeeee eeee (eeeeeeeeee eee eeeeeeeeeee; 8 e, 8.8 eeee) ee M8M (88 eM), 8,8-eeeeeee (88 eM), eee Me8M (88 eM), eee eee eeeeeeeee eeeeeee eee eeeeeee eee 88 eee. Mee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeeeeeee eeeeeee eeee 8 M ee MeMM (88 eM) eee 8 e. Mee eeeeeee eeeee eee eeee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (88 eM), eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe) eeeeeeee e eeeeeeeee eeeee; eeeee: 888 ee (88%); >88.8% ee; [α]M +888 (e 8, eeeeeee).

8-(8,8-Meeeeeee-8-eeeeeeeee)-8,8-eeeeeeee 8-Meeee (‌8‌, M8 = M; M8 = e-Me); Meeeeee Meeeeeeee:[‌88‌]

Me(MeMe)8 (8.888 eM, 888 ee, 8.88 eeee, 8 eeeee) eee eeeee ee e eeee ee (M,M)-MMM (8.88 eM, 8.888 e, 8.88 eeee, 8 eeeee) ee MM8Me8 eeeee M8. Mee eeeeeeeee eeee eeeeee eeee eee eeeeeee ee ee eee 8 eee. 8-(8,8-Meeeeeee-8-eeeeeeeee)-8,8-eeeeeeee (8.88 e, 8.88 eeee) eee eeeeeeeee ee MM8Me8 eee eeeee ee eeeeeee ee eee eeeeeee. Mee eeee eee eeeeeee ee ee eee e eeeeeee 8 eee eee eeee ee eeeeeee −88 eee −88 °M eee 88 eee. Meeeee eeeeeeeeeeeee (88 µM, 88.8 ee, 8.88 eeee, 8.8 eeeee) eee eeeee eee eee eeeeeee eee eeeeeee ee −88 °M eee 8 e. M8M (88 eeeee) eee eeeee ee eee eeeeeee, eeeee eee eeee eeeeeee ee −88 ee −88 °M eee 8 e eee eeeeeee ee eeeee ee eeee e eeeeeee 8 e eeee eeeeeeee. Meeeee eee eeeee eeeeeeee eeee eeeeeeeeee MM8Me8, eee eee eeeeeee eee eeeeeee eee e eeeeeee 8 eee. Mee eeeeeee eee eeeeeeee eeeee eeeeeee eeeeeeee eee eee Meeeee eee eeeeee eeee eeeeeee eeeeeeee ee MM8Me8. Mee eeeeeeee eee eeeeee eeee 8% ee Me8M8M8 eeeeeeeee eeee MeMe eee eeee eeee 8% ee MeMM eeeeeeeee eeee MeMe, eee eeee eeeee (MeMM8), eee eee eeeeeeee eeee eeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeee eeee eeeeeee. Meeee eeeeee eeeeeeeeeeeeee eeeeeeeee eee 8,8-eeeeeeee 8-eeeee eeeeeee; eeeee: 88.8 ee (88%).

References