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轴手性联芳基二醇通过氢键催化高度对映选择性的杂Diels-Alder反应。

Axially chiral biaryl diols catalyze highly enantioselective hetero-Diels-Alder reactions through hydrogen bonding.

作者信息

Unni Aditya K, Takenaka Norito, Yamamoto Hisashi, Rawal Viresh H

机构信息

Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637, USA.

出版信息

J Am Chem Soc. 2005 Feb 9;127(5):1336-7. doi: 10.1021/ja044076x.

Abstract

Axially chiral 1,1'-biaryl-2,2'-dimethanol (3, BAMOL) family of diols are highly effective catalysts for enantioselective hetero-Diels-Alder reactions between aminosiloxydiene 1 and a wide variety of unactivated aldehydes. The reactions proceed in useful yields and excellent enantioselectivities. The diols function in the same capacity as Lewis acids, by activating the aldehyde carbonyl group through hydrogen bonding.

摘要

轴手性1,1'-联芳基-2,2'-二甲醇(3,BAMOL)类二醇是氨基硅氧二烯1与多种未活化醛之间对映选择性杂环狄尔斯-阿尔德反应的高效催化剂。反应以有用的产率和优异的对映选择性进行。二醇通过氢键活化醛羰基,其作用与路易斯酸相同。

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