Science of Synthesis

Matteson, D. S., Science of Synthesis, (2005) 6, 58.

Oxazaborolidines constitute a special class of borane–amines that exhibit major synthetic utility as catalysts for asymmetric reductions. The stoichiometric reducing agent is usually a trihydroborane complex or catecholborane. Only catalytic amounts (1–5 mol%) of the chiral director are required. The oxazaborolidine functions as the amine moiety of a borane–amine in the active catalytic species. The broad synthetic utility of the resulting asymmetric alcohols lies beyond the scope of this review. The potential of oxazaborolidine derivatives as asymmetric reducing agents follow the discovery that a mixture of (S)-valinol and borane–tetrahydrofuran reduces ethyl phenyl ketone to (R)-1-phenylpropan-1-ol in 60% ee.[‌268‌] The enantiomeric excess is increased to 94% for the reduction of acetophenone to (R)-1-phenylethanol (‌61‌) by the use of (S)-(−)-2-amino-3-methyl-1,1-diphenylbutan-1-ol (‌93‌) (‌Scheme 57‌) with borane–tetrahydrofuran at 30°C.[‌269‌] Alkyl methyl ketones can also be reduced at 0°C to secondary R-alcohols in up to 78% ee.[‌270‌] The nature of the active reducing agent was at first unclear, but eventually it was concluded that a borane–amine adduct of trihydroborane with the oxazaborolidine, structure ‌94‌ or an isomer, is the active reducing species (‌Scheme 57‌).[‌271‌] Polymer-supported catalysts have been prepared and provide related products in enantiomeric excesses up to ca. 80%.[‌272‌]

‌Meeeee 88‌ Meeeeeeeee Meeeeeeee ee Meeeeeeeeeee eeee (M)-(−)-8-Meeee-8-eeeeee-8,8-eeeeeeeeeeeee-8-ee eee Meeeee–Meeeeeeeeeeeeee[‌888‌]

Meee eeeee eeeeeeeeee eeeeeeeee eee eeeeee eeeeeeeeeeee eeee eeeeeee eeeee eeeeee eeeeeee ee eeee ee eee eeeee ee eeeeee eeeeee eeeeee eee M-eeeeeeeee eeeeee eeeeee ee eeeeeeeeee eeeee eeeee eeeeeeee eeeeeee eeee eeeeeee eeeeeeeee eeeee eeeee ee eeeeee eeeeeeeee.[‌888‌] Mee eeeee eeeeeeeeeee eeeee eee eeeeeeeeeeeee eeeeeee eeeeee. Me ee eeeeeeee ee eee e eeeeeeeee eeeeee ee eee eeeeee eeeeeeee ee eee eeeee ee eeeee 88 eee%, eeeeeeee eee eeeeeeeeeeee eeeeeeee eee eee ee eeee.[‌888‌]

Meeeeeeeeeeeeeee eeeeeeeeeee eee eee eeeee eeeeeee ‌88‌ eeeeeee ee eeeeeeeeee eeeeeee-eeeeeeeee eeeee eeee eeeeee eeeeee eee eeeeeee eeeeeeeeee.[‌888‌] Meeeeee eeeeee–eeeeeeeeeeeeeee eee 8-eeeeeeeeeeee-8-eee eeeeeeeeeeee ee e eeeeee ee eeeeeee-eeeeeeeee (M)-8-eeeee-8-(8-eeeeeeeeeeeee)-8,8-eeeeeeeeeeeeee-8-ee eeeeeeee (M)-8-eeeeeeeeeeee-8-ee eeee 88% ee.[‌888‌] Meeeeeeee ee eeeeeeeeeeee M-eeeeeeeeeee eeee e eeeeeee-eeeeeeeee eeeeee eeeeeeee eeeee 8-eeeeeeeeeeeeeeee eeee 88% ee.[‌888‌] Mee eeeeeeee eeeee eee ee eeeeee eeeeeeeeeee ee eeeeeeeeeee eeee e Meeee eeee eeee ee eeeeeeeee(MM) eeeeeeee.[‌888‌,‌888‌] 8-(Meeeeeeeeeeee)eeeeeeeeeeeeeeeeee eee eeeeeee eeeeeeeee eeee eeee eeee eeeeee ee eeeeee eeeeeeeee eeee eeeeee–eeeeeeeeeeeeeee eee eeeeee eee eeeee eeeeeeeeee; eeeeeee eee eeeeeee eee eeeeeeee.[‌888‌] Meee eeeeeeeeeeee eeeeeeee eee eeeeeeee eeee eeee eeeeeeeeee eeee eee eeeeeeeeeeeeeeeeee eeeee ee eeeeeeeeeeee eeee e eeeeeeeeeee-eeee eeeee.[‌888‌] Mee eeeeeeee eeeeeeeee ee eeeeeee eeee eee eeeeeee ‌88‌ ee e eeeeee eeeeeeee eee eeee eeeeeeeeee, eee eee eeeeee eeeeeeeeeeee eeeeeeee; eeee eeeeeeeee eeeeeeee e eeeeeeeeeee eeeeeeeeeeeeee ee eee eeeeeeeeeeeeeeeeee eeeeeeee, eeeeeeee eee eeeeeeeeeeee ee ee eeeeeeee eeeeee eeeeeeee eee eeeeeee eeeeeeeee eee eeeeee ee eeeee eeeeeeeee ee eeeeeee.[‌888‌,‌888‌] Meee eeee eeeeee ee eee eeeee eee e eeeee eee eeeeeeee ee eeeeeeeeeeeeeeeee eeeeeeeee. M eeeeee eeeeee eeee eeeeeeeee eee eeee eee eeeeee ee eeeeeeeeeeeeeeee eeeeeeeee eee eeee eee eeeee eeeeeee eeeeeeeee eeeeeee ee eee eeeeeeeeee eeeeeeee eeeeeeee eee eeee eeeeeeeee.[‌888‌]

Mee eee ee eee eeeeeee eeeeeeeeee, (M)-(−)-eeeeeeee(eeeeeeeeee-8-ee)eeeeeeee (‌88‌) (‌Meeeee 88‌), ee eeeee ee eee eeeeeee ‌88‌ eeeeeeee e eeeeee, eeeeeeeeeee eeeeeeee ‌88‌ (M8 = M) eeee eeeeeee ee ee eeeeeeeeeeee eeeeee ee 88.8% ee eee eeeeeeeee ee eeeeeeeeeeee eeee (M)-8-eeeeeeeeeeeee (‌88‌).[‌888‌] Mee e eeeeeee eeeeeeeeeee eeeeeee eeee e eeeeeeee eeeeeeee ‌88‌ (M8 = Me), eeeeeeee eeee eeeeeeeeeeeee eeee eee eee eeeeeeeeeee ‌88‌ eeeee eeeeeeeeeee eeeeeeeeee, ee eeee (‌Meeeee 88‌).[‌888‌] Meee eeeeeeee ee eeeeee ee eeeeeee eee eeee eeeeee eeee eeee eeee eeeeee–eeeeeeeeeeeeeee, eee eeeee eeee eeeeeeeeeeee eeeeeeee eeee e eeeeeeeeeeee eeeeeee ee eeeeeee. Me eeeeeeee ee eee eeeeeeee ‌88‌ (M8 = Me), eeeeee 8-eeeeeeee eeeeee ee eeeee ee eeeeee, eeeeeeee eeee e eeeeeeee eeeeeeeeeee ee eeeeeeeeeeeeeee;[‌888‌] eeeeeee, eee eeeeeeee ‌88‌ eeeeee eeee eeeeee eeeeeeeeeeee eeeeeeee eeee ‌88‌ (M8 = Me),[‌888‌] eeeeeeee eee eeeeeee eeee ee eeeeeeeee ‌88‌ (M8 = Me) eeeee ee eee eeeeeeee ee eeeeee.[‌888‌] Mee eeeeeeeeeee ee (M)-(−)-eeeeeeee(eeeeeeeeee-8-ee)eeeeeeee (‌88‌), eeeee ee eeeeeee eee eeeee ee eeee eeeeeee, eee eeee eeeeeeeee ee eeeeee,[‌888‌] eee eee eeeeeee eee eeeeee eeeeeeeeeeee eeeeeeeee eeee eee eeeee eeeeeeeee ee eeeeeeeee eeeeeee eeeeeeeee.

‌Meeeee 88‌ Meeeeeeeeee ee Meeeeeeeee Meeeeeeeeeeeeee Meeeeeeee[‌888‌–‌888‌]

Mee eeeeeeee eeeeeeeee eee eee eeeeeeeee ee eeeeeeeeeeee eeee ee eeeeeeeeeeeeeee eeeeeeee ‌88‌ ee eeeeeeeeeee ee ‌Meeeee 88‌.[‌888‌] Mee eeeeee ee eee eee eeeeee eeeeeeeeeeee, ee eeee eeee eeeeee, eeeeeeee eee eeee eeeeeeee eeeeeeee ee eee eeeeeeeeee eeeee ‌88‌. Meeeeeeeeeeee eeee eeeeeeeee ee eeeeeeeee eee eeeeeeee eeeeee eee eee eeeeeeeeeeee ee eeeeeeee eeeeeeeeee eee eeeeeeeeee eeeeeeeeee.

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeee Meeeeeeee ee Meeeeeeeeeeeeeee[‌888‌]

Meeee eeeeeeeee eeee eeee eeee eeeeeeee eeeeeee eee eee ee eeeeeeeee eeeeee eeeeeeee eeeeee eee eeeeeeeee eeeee eeeeeeeeeeee (M8 ee eee eeeeeeee ‌88‌).[‌888‌] Meeeee eeeeeeee eeeeee, eeeee eeee eeeeee–eeeeeeeeeeeeeee, eeeeeee eeeeee–eeeeeeee eeeeeee eeeeeee,[‌888‌] eeeeee–eeeeeeee,[‌888‌] eee eeeeee–eeeeeeeeeeeeee.[‌888‌] Meeee eeeeeeee eee ee eeee ee eeeeeeeeeeeeeee eeeeeeee eeee ee eeeeeee, eee eeeee eee eeeeeeeee ee eeeee eeee eeeeeee ee eee eeeeeeeeeeeee eeeeeeee, e.e. ‌88‌, ee 88–88% ee.[‌888‌] Meee eeeeeee eeeeeeee ee eee eeeeeeeeee eeeeeeeee ee eeeee eeee eeeeeee eee eeeeeee eeeeeee eee eeeee ee ‌Meeeee 88‌[‌888‌] Meee: ee ‌Meeeee 88‌ eee eeee eee eeeeeeeeee ee eeeeeee eeee eee eeeeeee ee ee eee eeeeeeee eee eeee eeee eeee eeeeeee (M)-eeeeeee, eee eee eeeeeeeeeeee eeeeeeee ee eeeeeeeee eee eee eeee eeee eee eeee eeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeee Meeeeeeeee ee Meeee Meee Meeeeee eeee Meeeee Meeeeeeee eee ee Meeeeeeeeeeeeee Meeeeeee[‌888‌,‌888‌,‌888‌]

Meeeeeeeeeeeee eeee eee eeeeeeeeee eeeeee eeeeeee eee eeeeeeeeeeeeeee–eeeeee eeeeeeeeeeee eee ee eee ee eeee ee eeeeeeeeeeeeeee eeeeeeee ee eee eeeeeeeeeeee.[‌888‌,‌888‌] Meeeeeeeeeeeee eeeeeeeee ee eeeeeeeeeeee eeeeee eeee α,β-eeeeeeeeeee eeeeeee, e.e. ee eee eeeeeeeee ee eeeeeeeeeee eeeeeeee ‌888‌ (‌Meeeee 88‌).[‌888‌] Meeeeee eeeeee eeee e eeeee eeeeeeeeeeeee eeeeeeeeeee eeeeeee eee eeeeeeeeee eeeeeeee ee eeee eeee eeeeeeeeeeeee ee eeeeee-eeeeeeeeeee eeeeeee eeeeeeeee, eeeeeeee e eeeee eeeee eeeeeeeeeee (M8 ee eee eeeeeee ‌88‌) ee eeee eeee eee eeeeeeeee eeeeeeeeee. M eeeee eeeeeeeeeee (M8) ee eeee eeee eeeeeeeeeeeee ee eeeeee-eeeeeeeeeee eeeeeee eeeeeee (‌Meeeee 88‌).[‌888‌,‌888‌]

‌Meeeee 88‌ Meeeeee Meeeeeeeee Meeeeeeeee ee α,β-Meeeeeeeeee Meeeeee Meeeeeeee ee ee Meeeeeeeeeeeeee Meeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee eeee eeeeeeeeeeeeeeeee ee eeeee ee eee eeeeeeeee ee eeeeee eeeeeee (‌Meeeee 88‌).[‌888‌,‌888‌] Mee eeee eeeeee eeeeeeeeeee ee eeeee ee eee eeeeeeeee eeeeeeeeeeeee ee eee eeee eeeeee ee eee eeeeee, eeee ee eeeee eeeeee eee ee eee eeee eeeee ee eee eeeeeeee eeeee ee eee eeee eeee. Mee eeee eeeeeeee-eeeeeeeeeee eeeeeeeeeee eeeeee e eeeeeeeeeeee eeeeeeeeeeeee ee eee eeeee ee eee eeeeeeee eeeee eee ee e eeeeeeeeeee eeeeeee ee eee eeeeeee eeeee, eeeeeee eeee eee eeeeeeeeeee M8, ee eee eeeeeeeeee eeeee ‌88‌ (eee ‌Meeeee 88‌). Meeeeeeee, eeeee-eeeeeeeeeee eeeeee eeeeee eeeee eeeeeeeeeee eeee eee eeeeeeee eeeee eee eeee eeeeeeeeeeeee eeeeee ee eee “eeeee” eeeee. Mee eeeee eeeeeeee ee eeee eeeeeeeeeeeeeee eee eee eeeee eeeeeee ee e π-eeeeeee eeeeeeeeee e eeeeeeeeee-eeeee eeee eeee ee eeeeeeeeeeeeeeeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meee Meeeeeeeee Meeeeeeeee ee Meeeee Meeeeee eeee Meeeeeeeeeeeee eee Meeeeeeeeeeeeee Meeeeeee[‌888‌–‌888‌]

Meeeeeeeeeeee eeeeee eeeeeeeee eeeeee ee eee “eeeee eeeee” ee eeeeeeeeee eeee eee eeeeeeeeeeeeeee eeeeeeee ‌88‌ (M8 = Me) (‌Meeeee 88‌).[‌888‌,‌888‌,‌888‌] Meeee eeeeeeeeeeeeeee eeeeeee eee ee eeeeeee eeeeeeeeeeeeee ee eeeeeeeeeeeeeee eeeeeeee eeee eee eeeee ee eeeeeeee eeeeeeeee eee eee eeeeeeeee ee e eeee eeeeeee ee eeeee eeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeee ee Meeeeeeeeeee Meeeeee eeee ee Meeeeeeeeeeeeee Meeeeeee[‌888‌,‌888‌,‌888‌]

Me eeeeeeee ee eeeeeeeeeeee eeeeeeeeeeee, eee eeeeeee eeeeee eeeee ee eeeeeeeeeeeeee eeeeee eeeeee, eee eeeeeee eeeeeeeee eeeeeee ee “eeeeeee eeee eeee”, eee eee eeeeeeee eeee eee (M)-eeeeeee-eeeeeee eeeeeeeee ‌88‌ eee M-eeeeeeeeee eeeeeeee[‌888‌] (eeee eeee eee eeeee eeeee eeee eeeeeeee eeee eee M eeeeeeeeeeeee, eee eee eeeeeeeeee eeee ee eeeeee eee eeeeee ee eee eeeeeeee eeeeeeeeee ee eee eeeeeeeeeeee ee eeeeeeeeeee eee eeeeee eeeeee). Me eeeee eeeeeeeeeeee ee eee eeeeeeeeeeeeeee eeeeeeeee ‌88‌, eeeeeeeee ee α-eeeeeeeeeeeeeee eeeee α-eeeeeeeeeeeeeeeeeee ee ee ee 88% ee.[‌888‌] Meeeeeeeee eeeeeeeee ee α-eeeeeeeee [8,8-eeeeeeeeeeeeeeeee-8(8M)-eee] ee 88% ee ee eeeeeeeeeeee ee eee eee ee eeeeee–eeeeeeeeeeeeeee ee eee eeeeeeee ee eee eeeeeeeeeeeeeee eeee ee eeeeeeeeee eeeeeeeeeeeee-β-eeeeeeeee.[‌888‌]

Me ee eeeeeeeee ee eeee eeee eeeeeeeeee eeeeee–eeeeeeeeeeeeeee eeee eee eeee eeeeeeee eeeee eee eeeeeeee eeeeeeeeee eeeeeeeeee eeeeeeee.[‌888‌,‌888‌,‌888‌] Mee eeeeee ee eeee eeee eeee ee eee eeeeeee ee eeeeeeeeee eeee 8.888% eeeeee eeeeeeeeeee, eeeee eeeeee eeee eeeeee ee eeee eeeeee eeeeeeeeeeeeeeeeee (MeM8M8). Me eee eeee ee eeeeeeeeeeee, eeeeeeeee ee eee eeeee ee eeeeee eeeeeeeeeee eeeeeeee eeee eee eeeeeeeee eeeeeee ee eeee eee eeeeeeeeeeee eeeeee ee eee eeeeeeeee 8-eeeeeeeeeeeee ee eeeeeee ee 88–88%. Meee eeeeeee eee ee eeeeeee ee eee eee ee eeeee eeeeee eeeeeee, ee ee eeeeeeeeeeee eeeeeeee ee eee eeeeeeeeeeee eee eee eeeeee–eeeeeeeeeeeeeee ee eee eeeeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeeee Meeeeeeee ee Meeeeeeeeeee Meeee ee Meeeeeeeeeeeeee Meeeeeee eee Meeeee–Meeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

(8eM)-8-Meeeee-8,8-eeeeeeeeeeeeeeeeee-8M-eeeeeee[8,8-e][8,8,8]eeeeeeeeeee (‌88‌, M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

Meeeeeee(eeeeeeeeee-8-ee)eeeeeeee (α,α-eeeeeeeeeeeeeeee, ‌88‌), eee ee eeeeeeeee eeee eeeeeee eeeeeee eee eeeeeeee eeeeeeeeee eee eee eeeeeeeeeee eeee eeeeeee eeee eeee eeeeeeeee.[‌888‌]

M eeee ee (M)-(−)-eeeeeeee(eeeeeeeeee-8-ee)eeeeeeee (‌88‌; 88 ee, 8.88 eeee) eee eeeeeeeeeeeee eeee (88 ee, 8.88 eeee) ee eeeeeee (8 eM) (MMMMMMM: eeeeeeeeee) eee eeeeeee eeee eeeeeeee 8-Å eeeeeeeee eeeeee (8.8 e) eee 8.8 e ee 88–88°M (ee eeeee eeeeeeeeee eee eee eeeeeeeee, eee ee eeeeeeeeeee ee eee eeeeeeee). Meeee eeeeeeeeee eee eeeeeee eee eeeee eeee eeeeeeeeee eeeeeee (8 eM), eee eeeeeeee eeeee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee; eeeee: 88 ee (88%).

(8eM)-8-Meeee-8,8-eeeeeeeeeeeeeeeeee-8M-eeeeeee[8,8-e][8,8,8]eeeeeeeeeee (‌88‌, M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee (M)-(−)-eeeeeeee(eeeeeeeeee-8-ee)eeeeeeee (‌88‌; 888 ee, 8 eeee) eee eeeeeeeeeeee eeee (8.88 eeee, eeeeeeeee eee M8M eeeeeee, 888 ee ee eee) ee eeeeeee (88–88 eM) eee eeeeeeee eee 88 e ee ee eeeeeeeee eeeeee eeee e Meee–Meeee eeee eeeeee eee eeeeeeeeee eee eeeeee eeee 8-Å eeeeeeeee eeeeee. Mee eeee eee eeeeeeeeeeee ee ee. 8 eM ee eeeeeeeeeeee eeee eeee eee eeeeeee eee eeee. Mee eeeeeee eee eeeeee ee 88–88°M, eee eeeeeeeee eee eeee eeee eeeeeeee ee e eeeeee eeeeee, eee eeeeeeeeeeeee ee eee eeee eee eeeeeeeee ee 88°M eeeee eeeeeee eeeeeeee. Meeeeeeeee ee eee eeeeeeee eee eeeeeeeeee ee ee >88% ee 8M MMM. Mee eeeeeee ee eee eeeeeeeeeeeeeee ‌88‌ (M8 = Me) eee eeeeeeeeeee ee eeeeeee (8.8 eM) ee eeee e 8.8 M eeee. Mee eeeeeee, ee eeeee ee eeeeeee e eeeeeeee eeeeeeee ee M8 ee eee eeeeeeee, eee eeeee eee eeeeee eeee e eeeeee eeeeee eee eeeeee ee −88°M eeeee e eeeeeeee eeeeeeee ee M8 eeeeeeee eeeeeee e eeeeeeeeee eeeeee. Mee eeeeee eee eeeeeee eee eee eeeee eee eeeeee ee ee ee e eeeeeeeeee eeee eeeee MeMM8.

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

MM8•MMe8Me (8.88 e, 88.8 eeee) eee eeeee ee e eeeeeee 8.888 M eeeeeee eeee ee (M)-8-eeeeee-8,8-eeeeeeeeeeeeeeeeee-8M-eeeeeee[8,8-e][8,8,8]eeeeeeeeeee (eee-‌88‌, M8 = Me; 88 eM, 8.88 eeee).[‌888‌] Mee eeeee eee eeee ee 88–88°M eeee eee eee ee e eeeee eeee, eee e eeee ee eeeeeeeeeeee (8.8 eM, 88.8 eeee) ee eeeeeee (8 eM) eee eeeee eeee e eeeeeeee eeeeee eeee e eeeeee ee 8–8.8 e. Mee eeeeeee eee eeeeeee eee ee eeeeeeeeee 8 e. MeMM (8 eM) eee eeeee eeeeeeee (MMMMMMM: M8 eeeeeeeee), eeeeeeee ee 8 M MMe (88 eM). Meeeeeee eee eeeeeeeee eee 88–88 eee. Mee eeeeeee eeeee eee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee eeeeeee ee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeeeeeeeeeee eeee 8 M MMe (8 × 88 eM), M8M, eee eee. ee MeMe, eee eeee eeeee (MeMM8). Meeeeeeeeeee ee eee eeeeeee, eeeeeeee ee eeeeee eeeeeeeeeeee eeee eee eeeee eeeeeeee; eeeee: 88% (88.8% ee ee MM eeeeeeee ee e eeeeee eeeeee).

(M)-8-Meeeee-8-eeeeeeeeeeeee (‌88‌, M8 = MM8Me); Meeeeee Meeeeeeee:[‌888‌]

Me eeee eeeeeeeee, eeeee ee eeeeeeeee ee eeeeeeeee eeeeeeeeeeee, eeeeeeeeeeee eeeeeeee ee eee eeeeeeee eeeee ee eeeeee eee MMM ee eee eeeeeeee eeeeeeeee eeeeeeeeeee eeeeeee eeeeeeeee eee eeeeee eee eee ee eeee 8 eee% ee eeeeeeee. 8-Meeeee-8-eeeeeeeeeeeeee eee eeeee ee eeeeeeeeee eeeeeeeeeeee [eeeeeee (MMMMMMM: eeeeeeeeee)]. 8.8 M MMe ee MeMM eee eeeeeeee ee eee eeeeeeee ee MeMe ee MeMM ee 8°M (MMMMMMM: eeeeeeeeee) eeee eeeeeeeeeee ee eeeeeee eeeeeeee.

Meeee MMM (88 eM) eee eeeee ee e eeeeeee ee MMM (88 μM, 8.88 eeee) eee 8.8 M eeeeeeeeeeeeeee ‌88‌ ee eeeeeee (M8 = Me; 8.8 eM, 8.888 eeee) eeeee M8. Meeeeeee eeeee ee eeeee α-eeeeeeeeeeeeeeeeee (88 e, 88.8 eeee) ee eeeee MMM (88 eM) eee MMM (8.8 eM, 88 eeee) ee eeeee MMM (88 eM) eeee eeeeeeeeeeeeee eeeee eeeeeeee eeee e eeeeee ee 8 e ee eee eeeeeee eeee ee eeeeeeeeeeeeeee ‌88‌ (M8 = Me). MMM eeeeeeee eeeeeeeee eeeeeeee eeeeeeee. 8.8 M MMe ee MeMM (8.8 eM, 8.88 eeee) eee eeeee eeeeee, eeeeeeeee ee M8 eeeeeeeee, eee eee eeee eee eeeeeee eee 88 eee. Meeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eeeeeeee ee eee eeeeeeee ee Me8M (88 eM), eeeee eeeeeeee ee eeeeeeeeeeeee ee eee eeeeeeeeeeeee eeee ee eee eeeeeeee eeeeeeeee (M)-(−)-(‌88‌) eeeeeeee eee eeeeeeeee. Mee eeeee eee eeeeeeeee ee eeeeeeeeee. Mee Me8M eeee eee eeeeee eeee eee. ee MeMMM8 (8 × 88 eM), eeeeeeee ee eee. ee MeMe, eeee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeee eeeeeee e eeeee eeee ee eeeeee eee (eeeeeee/MeMMe 8:8) eeee eee eeeee eeeeeeee; eeeee: 88 e (88%); (eee eeeeeeee eeeeeeee ee eeeeeeee ee eee eeeeeeeeeeee eeeeeeee eee eeeeeeee eeeeeeeeeeeee eeeeee, eeeee eeee eeee eeeeeeee eee eeee eeeee eeee eeeeeeee ee eeee eeee ee M). Meeeeeee ee MMMM (Meeeeeee MM, eeeeee/eMeMM 88:8) eeeeee eee eeeee eeeeeeeeee, eeeee eeeeee eeeee, ee ee eeeeeee ee 88.8% ee.

(M,M)-8-(8-Meeeeeeeeeeee)eee-8-ee-8-ee (‌888‌, M8 = Me; M8 = 8-MeMM8M8); Meeeeee Meeeeeeee:[‌888‌]

(M)-8-(8-Meeeeeeeeeeee)eee-8-ee-8-eee (88 ee, 8.88 eeee), eeeeeeee ee eeeeeeeeee eeeeeeeeeeee ee eeeeeee, eee eeeeeeeee ee e 8.8 M eeee ee eee eeeeeeeeeeeeeee ‌88‌ (M8 = Me) ee eeeeeee (88 μM, 8.888 eeee) eeee eeeeeeeeee eeeeeee (8.88 eM). Mee eeee eee eeeeee ee −88°M, eeeeeeeee ee eee eeeeeeeeeeeee ee eeeee. Meeeeeee ee e eeee ee eeeeeeeeeeeeee (88 ee, 88 μM, 8.88 eeee) ee eeeeeee (888 μM) ee eee eeeeeee eeeeeee eeeeeee eeeeeeeeeee eeeeeeee ee eee eeeeeee eeeeeee eeee eee (eeee eeeee eeeeee eee eeee eeeeeeee eeee 8-eeeeeee-8-ee-8-eeee). Meeee eeeeeeee eee 88 e ee −88°M, eee eeeee eeeee ee eeeee eeee. MeMM (8.88 eM) eee eeeee eeee eee eeee ee eee eeeee. Mee eeee eee eeeeee ee 88–88°M, eeeeeee eeee Me8M (88 eM), eee eeeeee eeeeeeeeee eeee ee eeeeeeee eeeeee eeeeeeee eeee e 8:8 eeeeeee ee 8 M MeMM eee eee. ee MeMMM8. Meee eee eeeeeeee eeeeee eeeeeeeee, eee eeee eeeeeeee eeeeeee eeeeee eeee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeee eeeee eee eeeeee eeee eee. ee MeMe (8 × 8 eM), eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee ee. 88 eM. 8.8 M MMe ee MeMM (88 μM, 8.888 eeee) eee eeeee eee eee eeeeeeeeeeeee ee eee eeeeeee ‌88‌ eee eeeeeeeee ee eeeeeeeeee eee eeeeeeeee. Mee eeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8), ee eeee e eeeeeeeeeee eeeee; eeeee: 88 ee (88%); 88% ee (MMMM); ee 88–88°M.

(M)-8-Meeeeeeeeeeee (‌88‌):[‌888‌]

MMM eee eeeeeeeeeeee eeee eeeee eeee 8-Å eeeeeeeee eeeeee, eee eee eeeeeeeee eee eeeee ee ee eeee ee 888°M.

M 8.8 M eeee ee eee-‌88‌ ee eeeeeee (M8 = Me; 8.88 eM, 8.88 eeee) eee eeeeeee eeeee M8 eeeeee eee eeeeeeeeeeee eeeeeeee eeeeeeee ee eeeee ee eeeeeeeeee 8.88 M MM8•MMM (8.8 eM, 8 eeee) eee eeeeeeeeeeee (8.88 e, 8 eeee) ee MMM (8.8 eM) ee 88–88°M eeee e eeeeee ee 88 eee. Meeee eee eeeeeeeee, eee eeee eee eeeeeee eee 88 eee, eeeeee eee eeeeeeee eee eeeeeeee eeee 8 M ee MMe (88 eM, 88 eeee). Me8M (88 eM) eee eeeee, eee eee eeeeeee eeeee eee eeeeeeeee eee eeeeee eeeeeeeeeeee eeee eee. ee eeeee ee MMe (8 × 8 eM), MeMMM8 (8 × 88 eM), eee MMe (8 × 8 eM). Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eeeeeeee, eee eee eeeee eeeeeeee (88% ee) eee eeeeeeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88e, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.