Enantioselective Synthesis of Chromans with a Quaternary Stereogenic Centre through Catalytic Asymmetric Cascade Reactions

被引：13

作者：

Hua, Qiu-Lin ^{[1
]}

Li, Chao ^{[1
]}

Wang, Xu-Fan ^{[1
]}

Lu, Liang-Qiu ^{[1
]}

Chen, Jia-Rong ^{[1
]}

Xiao, Wen-Jing ^{[1
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China

来源：

ACS CATALYSIS | 2011年 / 1卷 / 03期

基金：

美国国家科学基金会;

关键词：

organocatalysis; cascade reaction; Michael addition; heterocycle; chromans; DOUBLE-MICHAEL ADDITION; N-HETEROCYCLES; CONJUGATE ADDITION; SULFUR YLIDES; ALPHA; BETA-UNSATURATED KETONES; COUMARIN DERIVATIVES; NATURAL-PRODUCTS; CHIRAL CHROMANS; VITAMIN-E; THIOUREA;

D O I：

10.1021/cs100161k

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A highly enantioselective cascade reaction of benzotriazoles with nitroolefin-cotaining enonates catalyzed by a base/acid bifunctional organocatalyst has been developed. This cascade sequence affords efficient access to densely functionalized chiral chromans with a quaternary stereogenic center in high yield (up to 91%) with excellent enantioselectivity (up to 96% ee) and diastereoselectivity (up to 96:4 dr). The reaction itself features simple experimental procedures under benign conditions and is completely atom economic in character.

引用

页码：221 / 226

页数：6

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