Enantioselective Organocatalytic Michael Addition of Malonates to α,β-Unsaturated Ketones

A novel type of primary amine thiourea organocatalysts derived from 1,2-diaminocyclohexane and 9-amino (9-deoxy) cinchona alkaloid was developed into asymmetric Michael addition of malonates to enones. A series of cyclic and acyclic enones could react very well with different malonates in the presen...

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Bibliographic Details
Published in:Organic letters 2009-02, Vol.11 (3), p.753-756
Main Authors: Li, Pengfei, Wen, Shigang, Yu, Feng, Liu, Qiaoxia, Li, Wenjun, Wang, Yongcan, Liang, Xinmiao, Ye, Jinxing
Format: Article
Language:English
Subjects:
Cinchona Alkaloids - chemistry
Ketones - chemical synthesis
Ketones - chemistry
Malonates - chemistry
Molecular Structure
Stereoisomerism
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Summary:A novel type of primary amine thiourea organocatalysts derived from 1,2-diaminocyclohexane and 9-amino (9-deoxy) cinchona alkaloid was developed into asymmetric Michael addition of malonates to enones. A series of cyclic and acyclic enones could react very well with different malonates in the presence of 4 with 0.5−10 mol % catalyst loading affording chiral Michael adducts with excellent yields and ee values.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol802892h