Organocatalytic enantioselective construction of nitrocyclohexanes containing multiple chiral centres via a cascade reaction

被引:56
作者
Rajkumar, Sundaram [1 ]
Shankland, Kenneth [1 ]
Brown, Geoffrey D. [2 ]
Cobb, Alexander J. A. [1 ]
机构
[1] Univ Reading, Div Pharmaceut Chem, Sch Pharm, Reading RG6 6AD, Berks, England
[2] Univ Reading, Sch Chem, Reading RG6 6AD, Berks, England
关键词
QUATERNARY STEREOCENTERS; CONJUGATE ADDITION; MICHAEL ADDITION; DERIVATIVES; CYCLIZATION; OXINDOLES; CATALYSTS; MALONATE; ESTERS;
D O I
10.1039/c1sc00592h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The stereoselective construction of complex molecules with multiple stereogenicity in a single step represents an extremely useful, but challenging approach to complexity in chemical synthesis. The development of organocatalytic cascade processes has proven useful in these studies, but reports where four or more stereocentres are created in a single step from just two achiral reagents are rare. Herein we report the development of a novel asymmetric domino Michael-Michael reaction between nitrohex-4-enoates and nitro-olefins to generate cyclohexanes of high complexity, including one with a quaternary centre, and three with five contiguous stereocentres. This methodology provides access to a range of useful nitrocyclohexane derivatives, including a novel class of alpha-lycorane-like structures.
引用
收藏
页码:584 / 588
页数:5
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