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
收藏
页码：221 / 226
页数：6
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