Science of Synthesis

Amatore, M.; Aubert, C.; Malacria, M.; Petit, M., Science of Synthesis Knowledge Updates, (2012) 3, 109.

The asymmetric ring opening of epoxides has been widely described. With meso-epoxides, this reaction offers an elegant route to useful and enantiomerically pure synthons; however, access to highly enantioenriched epoxides is limited. The asymmetric ring-opening chemistry is a practical method for the kinetic resolution of racemic terminal epoxides, providing the desired enantiopure compounds with high yields. Various cobalt–salen complexes have been employed for these two strategies (‌Scheme 108‌).[‌391‌,‌392‌] Moreover, these strategies can be used with success for the asymmetric synthesis of small drugs such as (R)-mexiletine[‌393‌] or (+)-goniodiol.[‌394‌]

‌Meeeee 888‌ Meeeeeeeee eee eee Meeeee-Meeeeeeee Meee Meeeeee ee Meeeeeee[‌888‌,‌888‌]

α-Meeeeee ee α-eeeeee eeeeeeee eee ee eeeeeeee ee eeeeeee eeeeeeeeee ee eeeeeeee eeeeeeee eeee eeeeeeee eeeee eeeeee–eeeee eeeeeeeee.[‌888‌,‌888‌] Mee eeeeeeeee ee eeeeeeeeeeeeeeee eeeeeeee α,α-eeeeeeeeeeeee β,γ-eeeee eeeeee eeee ee (M)-‌888‌ eee eeee eeee eeeeeeeee eeeee eeeeeeeeee eeeeeee eeeeeeeeee ee eee eeeeeeeeeeeee eeeeeee α,α-eeeeeeeeeeeee eeeeeeee (‌Meeeee 888‌).[‌888‌]

‌Meeeee 888‌ Meeeee-Meeeeeeee Meeeeeeeee Meeeeee Meeeeeeeee ee e Meeeeee α,α-Meeeeeeeeeeee Meeeeee[‌888‌]

Meeeeeee eeeeeeeeeeee eee ee eeeeeeee ee eeeee eeeeeee-eeeeeee eeeeeeeee eeeee eeeeee–eeeee eeeeeeeee.[‌888‌] Me eeee eee, eeeeee ee eeeeeeee eeeeeeeeeee eeeeeeeee ee eeeeeeee eeeeeeee eeee eeeeee eeeeeeee. Meeeeeeeeee eeeeeeeee eeee eeee eeeeeeeee eeeee ee eeeee eeeeeeeeee, eeee ee eee eeeeeeeeeeeeeeee eeeeeeeeeeee eeeeeeeeeeee ee eeee- eee eeeeeeee eeeeeeee eeee eeeeeee eeeeeeee ee eeeeeeee eeeeee.[‌888‌] Meeeeeeeeeeeeee eeeeeee eeeee eeeeeeee, e.e. ‌888‌, eee ee eeeeee eeeee eee eeee eeeeeeeee eeeeeee eee eeeeeeeee eeeeeeeeeeeee eee eee eeeee eeeeeeeee ee eeeeeeeeeee eeeeeeee eeeeeeeeee eeee ee ‌888‌ (‌Meeeee 888‌).[‌888‌,‌888‌]

‌Meeeee 888‌ Meeeeeeee ee ee Meeeeeeeeeeeeeee Meeeeeee Meeeeeee Meeeeeeee eeee e Meeeeee Meeeeee[‌888‌]

Me eeeeeee eeeeee eee eeee eeeeeeee eee eee eeeeeeeeeeeeee eeeeeeeeee eeee eeeeeee ee eeeeeeee ‌888‌ eeee eeeeee–eeeee eeeeeeeee, eeeeeeeee e eeeeeeeeeeeeeee eeeeee ee eeeeeeeeeeeeeeee eeee eeeeeeeeeeeeeee eeeeeeeeeee ‌888‌ (‌Meeeee 888‌).[‌888‌] Meee eeee eeeeeeeeeeeee eeeeeeee eeeeeeeeee eeeeee–eeeee eeeeeeeee eee eeee eeeeeeee eeeeeeeeeee eee eeeeeeeeeeeeeeee eeeeeeeeeeeeee ee eeeeeeee.[‌888‌]

‌Meeeee 888‌ Meeeeeeeeeeeeeee Meeeeeeeeeeeee Meeeeee ee Meeeeeee[‌888‌]

‌Meeeeeeeeee 888‌

Meeeeeeeeeee Meeeeeeee

Meeee (M)-8-Meeee-8-(eeeeee-8-ee)eeeeeeeee [(M)-‌888‌]; Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee eeeeeeeeee ee [(M,M)-M,M′-eee(8,8-ee-eeee-eeeeeeeeeeeeeeeee)eeeeeeeeeee-8,8-ee­eeeee]eeeeee(MM) (88 ee, 88 μeee) ee eeeeeee (8 eM) eee eeeee e eeee ee 88% MeMM ee eeeeeee (88 μM) eee eee eeeeeee eee eeeeeee eeeee eee eee 8 e. Mee eeeeeee eee eeeeeee eeee M8 eee eee eeee eeeee eeeeeee eee eeeee eeeee eeeeee eee eeee eeeeeeee ee eee eeeeeee eeeeeeeeee eeeeeeee. Meeeeee eeeee 8-eeeee-8-(eeeeee-8-ee)eeeeeeeee (eee-‌888‌; 8.888 e, 8.88 eeee) eee M8M (88 μM, 8.8 eeeee) eeee eeeee ee eee eeeeee Me eeeeeeee eeeeeeee eeeeeeeeee (88 ee, 8 eee%) eee eeeeeee eee 88 e ee ee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:8) ee eeeeee eeeee (M)-8-eeeee-8-(eeeeee-8-ee)eeeeeeeee [(M)-‌888‌]; eeeee: 88%; 88% ee.

(M)-8-Meeee-8-(8-eeeeeeeeeeeeeeeeeee)eeeeeeeee (‌888‌); Meeeeee Meeeeeeee:[‌888‌]

M 8-eM eeee eeeeeeee eeee e eeeeeee eee eee eeeeeee eeee [(M,M)-(+)-M,M′-eee(8,8-ee-eeee-eeeeeeeeeeeeeeeee)eeeeeeeeeee-8,8-eeeeeee]eeeeee(MM) (88.8 ee, 88 μeee, 8.88 eeeee). Mee eeeeeeee eee eeeeeeeee ee MM8Me8 (8.8 eM) eee eeeeeee eeee MeMM (88 μM, 8.8 eeee). Mee eeee eee eeeeeee ee ee eeee ee eee eee 88 eee, eeeeee eeeee eeee eee eeeee eeeeeee eeee eeeeee-eee ee eeee eeeee. Mee eeee eee eeeeeeeeeeee ee eeeeeee eeeee eeeeeee eeeeeeee ee eeeee eeeee (M,M)-eeeee–eeeeee eeeeeeee ee e eeeee eeeee, eeeee eee eeee eeeeeee eeeeeee eeeeeeeeeeee. Mee eeeeeeee eeeeeee eee eeeeeeeee ee e eeee ee eeeeeee 8-eeeeeeeeeeee (888 ee, 8.8 eeee) ee MMM (88 μM) ee ee. Mee eeeeeeee eeee eee eeeeee ee 8 °M eee M8M (88.8 μM, 8.88 eeee, 8.88 eeeee) eee eeeee eeeeeeee ee eee eeee. Mee eeeeeee eee eeeeeee ee ee eee 8 e, eeeee eeeee eeee eeee-eeeee [(8-eeeeeeeeeee)eeeeeeee]eeeeeeeee (888.8 ee, 8.88 eeee, 8.8 eeeee) eee MMM (888 μM) eeee eeeee. Mee eeeeeee eee eeeeeee ee ee eee 8 e. Me eee eeeee eeeeeee eeee eeeee MMMM (88 ee) eee MM8Me8 (8 eM), eee eee eeeeeeeee eeeeeee eee eeeeeeee eeeeeee e eee ee eeeeee eee (88 e). Mee eeeeee eee eee eeeeee eeee MeMMe/eeeeeee (8:8; 888 eM) eee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee ‌888‌ (eeeee: 88%; 88% ee). Mee eeeeeee ‌888‌ eee eeeeeeeee ee MM8Me8 (8 eM) eee eeeeee ee 8 °M. MMM (8 eM) eee eeeee eeeeeeee eee eee eeeeeee eee eeeeeee ee eeee ee ee eeee eeeeeeee. Meeee 8.8 e, eee eeee eee eeeeee ee 8 °M eee eeeeeee eeee Me8M (88 eM) eee eee. ee MeMMM8 (88 eM). Mee eeeeeee eeeee eee eeeeee eeee eeeee (88 eM), eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeee eeee M8 eee eeeeeeeee ee MM8Me8 (8 eM) eee eeeeeeee (888 μM, 8.8 eeee, 8 eeeee). Me8M (888 ee, 8.8 eeee, 8.8 eeeee) eee MMMM (88.8 ee, 8.8 eeee, 8.8 eeeee) eeee eeeee. Mee eeeeeee eee eeeeeee ee ee eee 88 eee, eee eeee eeeeeee eeee Me8M (88 eM) eee eee. ee MeMM8 (88 eM). Mee eeeeeee eeeee eee eeeeee eeee eee. ee MeMM8 (88 eM) eee eeeee (88 eM), eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeeee ee MMM (8 eM) eee eee. ee M8MM8 (8 eM), eee eeeeee ee eeeeee eee 8 e. Mee eeeeeee eee eeeeeee eeee Me8M (88 eM) eee M8M (88 eM). Mee eeeeeee eeeee eee eeeeee eeee eeeee (88 eM), eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (MeMMe/eeeeeee 88:88) ee eeee ‌888‌ ee e eeee eeeeee eee; eeeee: 888.8 ee (88%); >88% ee (eeeeeeeeee ee eeeeee MMMM). Meeeeee eeeee (eeee eeeeeeeeeeeeeeeee): 88%.

Meeeeeeeeee 8-(Meeeeeeeeeeeeee-8-ee)eeeeeeee ‌888‌; Meeeeee Meeeeeeee:[‌888‌]

M 88-eM eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeeee eee eee eeeeeee eeee [(M,M)-(+)-M,M′-eee(8,8-ee-eeee-eeeeeeeeeeeeeeeee)eeeeeeeeeee-8,8-eeeeeee]eeeeee(MM) (888 ee, 8.88 eeee). MM8Me8 (88 eM) eee eeeee eee eee eeeeeee eee eeeeeee eeeee eeeeeeee eeeeeeeeeee eee eeee eeeeeeee. MeMM (888.8 μM, 8.88 eeee) eee eeeee eee eee eeeeeeeee eeeee eeee eee eeeeeee eeeeeeeeee eeee ee eee eee eee 8 e. Meeeeee eee eeeeeee eee eeeeee eeeeeeeeeee eeeeeeee ee eeee eeeeee. Mee eeeee eeeeeee eee eeeeeeeee ee eeeeeee eee eeeeeeeee ee eeeeeeeeee ee e Müeeeee eeeeee. Mee eeee eee eeeeee eeee eeeeeee eeeee eee eeeeeeee eeeeeeee eeeee. Mee eeeeeeee eeeee (M,M)-eeeee–eeeeee eeeeeee eee eeeeeeeee ee MM8Me8 eee eee eeee eee eeeeeeee eeeeeee eeeee eeee ee eeeeee eee eeeeeeeee eeeeeeeeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee 8-(eeeeee-8-ee)eeeeeee ‌888‌ (8.8 eeee, 8.8 eeeee) eee eee (M,M)-eeeee–eeeeee eeeeeee (8.8 ee, 8.888 eeee, 8 eee%) eeee eeeee ee e eeee. Mee eeeeeee eee eeeeeee eeeee eeeeeeeeee ee eee eeeeeeee, ee eeeee eeeee Meeeeeeee eeeee eeeeeeeee MMM (e eeeeee-eeeee eeeeeeeeeeee eeee eeeeeeeeee; 88 ee) eee MeMMe (8.8 eM) eeee eeeee. Mee eeeeeeeeee eee eeeeeee eee 8 e, eeeeeeee, eee eeeeeeeee ee eeeeeeeeeeee ee eeeeee eeeeeeeeeeeeee (MeMMe/eeeeeee) ee eeeee eee eeeeeee eeeeeee ‌888‌.

References