Iminium-Allenamine Cascade Catalysis: One-Pot Access to Chiral 4H-Chromenes by a Highly Enantioselective Michael-Michael Sequence

被引:134
作者
Zhang, Xinshuai [1 ]
Zhang, Shilei [1 ]
Wang, Wei [1 ]
机构
[1] Univ New Mexico, Dept Chem & Biol Chem, Albuquerque, NM 87131 USA
基金
美国国家科学基金会;
关键词
alkynal; cascade reactions; enantioselectivity; Michael addition; organocatalysis; DIELS-ALDER REACTION; ASYMMETRIC-SYNTHESIS; NUCLEOPHILIC-ADDITION; FACILE CONSTRUCTION; ALLENES; PALLADIUM; ALCOHOLS; ESTERS; 2-AMINO-4H-CHROMENES; CYCLOADDITION;
D O I
10.1002/anie.200906050
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chemical Equation Presented Taking the Michael-Michael: A cascade Michael-Michael reaction of aryl or alkyl alkynals, involving an unprecedented iminium - allenamine sequence, is efficiently catalyzed by a chiral diphenylprolinol TBDMS ether, and affords highly functionalized 4H-chromenes in high yields. TBDMS = tert-butyldimethylsilyl. © 2010 Wiley-VCH Verlag GmbH &. Co. KGaA,.
引用
收藏
页码:1481 / 1484
页数:4
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