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
收藏
页码：130 / 135
页数：6
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