Facile Construction of Vicinal Quaternary and Tertiary Stereocenters via Regio- and Stereoselective Organocatalytic Michael Addition to Nitrodienes

被引：37
作者：
Chauhan, Pankaj [1 ]
Chimni, Swapandeep Singh [1 ]
机构：
[1] Guru Nanak Dev Univ, UGC Ctr Adv Studies Chem, Dept Chem, Amritsar 143005, Punjab, India
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 17期
关键词：
Cinchona alkaloids; Michael addition; nitrodienes; organocatalysis; quaternary stereocenter; ENANTIOSELECTIVE CONJUGATE ADDITION; ASYMMETRIC-SYNTHESIS; STEREOCONTROLLED CREATION; STRUCTURAL CONFIRMATION; ORGANIC CATALYSIS; AERUGINOSIN; 298-A; NITROOLEFINS; ALDEHYDES; THROMBIN; NITROALKANES;
D O I：
10.1002/adsc.201100618
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A highly regio- and stereoselective protocol for the synthesis of vicinal quaternary and tertiary stereocenters has been developed. The 6'-OH Cinchona alkaloids (BnCPN or BnCPD) at low catalyst loading (0.5-5 mol%) catalyze the Michael addition of trisubstituted carbon nucleophiles to nitrodienes in good to excellent yield (up to > 99), high enantioselectivity (up to 99% ee) and high diastereoselectivity (up to > 99:1 dr) under mild reaction conditions.
引用
收藏
页码：3203 / 3212
页数：10
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