Origins of Enantioselectivity in Proline-Catalyzed Friedlander Condensations of 4-Substituted Cyclohexanones

被引：4

作者：

Li, Le ^{[1
]}

Seidel, Daniel ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA

来源：

SYNTHESIS-STUTTGART | 2011年 / 12期

关键词：

Friedlander synthesis; quinolines; amino aldehydes; organocatalysis; proline; DIRECT ALDOL REACTION; MANNICH-TYPE REACTIONS; ASYMMETRIC-SYNTHESIS; CONFORMATIONAL EQUILIBRIA; AMINO-ACIDS; ENAMINE; STEREOSELECTIVITY; DESYMMETRIZATION; ORGANOCATALYSIS; PYRROLIDINE;

D O I：

10.1055/s-0030-1260526

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Computational studies reveal the origin of the enantioselectivity in proline-catalyzed Friedlander condensations of 4-substituted cyclohexanones with aminobenzaldehydes. Both the catalyst structure and the nature of the substituent on cyclohexanone play important roles in this desymmetrization process. The model presented herein provides a satisfying explanation for the vastly different selectivities that are observed for 4-phenylcyclohexanone versus 4-(tert-butyldimethylsilyloxy)cyclohexanone.

引用

页码：1853 / 1858

页数：6

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