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催化对映选择性多米诺氧杂-迈克尔/羟醛缩合反应:苯并吡喃衍生物的不对称合成

Catalytic enantioselective domino oxa-michael/aldol condensations: asymmetric synthesis of benzopyran derivatives.

作者信息

Sundén Henrik, Ibrahem Ismail, Zhao Gui-Ling, Eriksson Lars, Córdova Armando

机构信息

Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden.

出版信息

Chemistry. 2007;13(2):574-81. doi: 10.1002/chem.200600572.

DOI:10.1002/chem.200600572
PMID:17039558
Abstract

The first direct organocatalytic asymmetric domino oxa-Michael/aldol condensation reaction is presented. The unprecedentedly simple, chiral, pyrrolidine-catalyzed asymmetric domino reactions between salicylic aldehyde derivatives and alpha,beta-unsaturated aldehydes proceed with high chemo- and enantioselectivities to give the corresponding chromene-3-carbaldehyde derivatives in high yields and with ee values of 83-98%.

摘要

首次报道了直接的有机催化不对称多米诺氧杂-迈克尔/羟醛缩合反应。水杨酸醛衍生物与α,β-不饱和醛之间前所未有的简单、手性吡咯烷催化的不对称多米诺反应,以高化学选择性和对映选择性进行,高产率地得到相应的色烯-3-甲醛衍生物,对映体过量值为83-98%。

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