A highly regio- and enantioselective organocatalyzed Michael addition of malonates to nitrodienes

被引：11
作者：
Chowdhury, Raghunath [1 ]
Vamisetti, Ganga B. [1 ]
Ghosh, Sunil K. [1 ]
机构：
[1] Bhabha Atom Res Ctr, Div Bioorgan, Bombay 400085, Maharashtra, India
来源：
TETRAHEDRON-ASYMMETRY | 2014年 / 25卷 / 6-7期
关键词：
ASYMMETRIC CONJUGATE ADDITION; 1,3-DICARBONYL COMPOUNDS; CYCLIC-KETONES; METHYL KETONES; NITROOLEFINS; NITROALKENES; CATALYSIS; ESTERS; UREA;
D O I：
10.1016/j.tetasy.2014.02.007
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
An organocatalyzed direct Michael addition of unsubstituted/substituted malonates, acetoacetate, or acetylacetones to conjugated nitrodienes using a cinchona alkaloid-based thiourea catalyst is disclosed. The addition products were formed in high yields and regioselectivity. The enantioselectivities of the addition products were high in most cases and could significantly be improved upon by a single recrystallization. The addition products easily undergo chemoselective nitro group reduction and subsequent lactamization with a high synthetic potential. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：516 / 522
页数：7
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