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1.2.1.9.6 Enantioselective Kabachnik–Fields Reactions

DOI: 10.1055/sos-SD-210-00157

Zefirov, N. S.; Matveeva, E. D.; Shuvalov, M. V.Science of Synthesis: Multicomponent Reactions, (20141288.

Considerable research efforts have been focused upon the development of enantioselective three-component Kabachnik–Fields reactions and there are two different approaches for the realization of this goal. The first applies optically active components to the reaction and the second utilizes an optically active catalyst. Examples are given in Scheme 12.[‌95‌‌100‌]

Meeeee 88 Meeeeeeeeeeeeeee Meeeeeeee–Meeeee Meeeeeeee[‌88‌‌888‌]

Meeeeeeeeee 88

Me8 Meeee (%) ee (%) Mee
Me 88 88 [‌888‌]
8-M8MM8M8 88 88 [‌888‌]
8-MM8M8 88 88 [‌888‌]
8-Mee 88 88 [‌888‌]
8-Mee 88 88 [‌888‌]
8-eeeeeeee 88 88 [‌888‌]
8-M8MM8M8 88 88 [‌888‌]
8-MeMM8M8 88 88 [‌888‌]
8-MeM8M8 88 88 [‌888‌]
8-MeM8M8 88 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee [(M)-8-[(eeee-Meeeeeeeeeeeee)eeeee]-8-{[(M)-8-eeeeeee-8-eeeeeeeeeee]eeeee}eeeeeeeee-8-ee]eeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee eeeeeeeee-8-eee 88 (888 ee, 8.888 eeee) ee MeMM (8 eM) eee eeeee (M)-8-eeeeeee-8-eeeeeeeeeeeeeeee (888 ee, 8.88 eeee), MeMM (888 µM, 8.88 eeee), eee MeMM8 (88 ee, 8.88 eeee). Meeee eeeeeeee eee eeeeeee ee 88 °M eee 8 e, M(MMe)8 (888 µM, 8.88 eeee) eee eeeee eee eee eeeeeeeee eeeeeee eee eeeeee ee 88 °M eee 88 e. Me eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eeeee ee MM8 (8 eM) eee eeeee ee eee eeeeeee. Mee eeeeeeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMM/MM8Me8 8:88) ee eeeeee eeee eeeeeeeeeeeeeeee 88 ee ee eeeeeeeeeee eeeeeee ee eee eeeeeeeeeeeee ee e 88:88 eeeee ee eeeeeeeeee ee 88M MMM eeeeeeeeeeee; eeeee: 888 ee (88%).

Meeeeeee {Meee[(8-eeeeeeeeeeeee)eeeee]eeeeee}eeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌888‌]

M,M′-Meeeeee 88 (8.88 eeee), Me(MMe)8 (8.88 eeee), ee eeeeeeee (8.8 eeee), eee 8-eeeeeeeeeee (8.8 eeee) eeee eeeee ee e eeee eeee eeeee M8. Meee, MMM (8.8 eM) eee eeeee eee eee eeeeeee eee eeeeeee ee 88 °M eee 8 e. Meeeeeee eeeeeeeeeee (8.8 eeee) eee eeeee ee eee eeeeee (−88 °M) eeeeeee, eeeee eee eeee eeeeeee eee e eeeeeee 88–88 eee. Mee α-eeeee eeeeeeeeeeee eeee eeeeeeee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeeeee eeeee 8:8 ee 8:8).

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