Reversal of enantioselectivity induced by the achiral part of an organocatalyst in a Diels-Alder reaction

被引：10

作者：

Tawde, Trupti S. ^{[1
]}

Wagh, Swapnil J. ^{[1
]}

Sapre, Jai V. ^{[1
]}

Khose, Vaibhav N. ^{[1
]}

Badani, Purav M. ^{[1
]}

Karnik, Anil V. ^{[1
]}

机构：

[1] Univ Mumbai, Dept Chem, Bombay 400098, Maharashtra, India

来源：

TETRAHEDRON-ASYMMETRY | 2016年 / 27卷 / 2-3期

关键词：

ASYMMETRIC CYCLOADDITION; ALPHA-NITROPHOSPHONATES; TRANSFER HYDROGENATION; CONJUGATE ADDITION; HENRY REACTION; ALDOL REACTION; ANTHRONE; THIOUREA; BIS(THIAZOLINE); BIS(OXAZOLINE);

D O I：

10.1016/j.tetasy.2016.01.002

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new series of chiral organocatalysts was developed by attaching achiral heterocyclic units via a methylene group to (S)-2-hydroxyethylbenzimidazole for the asymmetric Diels-Alder reaction between anthrone enolate and maleimides. While organocatalysts with pyridine, quinoline, and 1,3,4-oxadiazole achiral heterocyclic subunits gave Diels-Alder adducts with an (S,S)-configuration, the organocatalyst with a benzotriazole subunit caused formation of the (R,R)-configuration for the Diels-Alder adducts (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：130 / 135

页数：6

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