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Org Lett. 2009 Feb 5;11(3):753-6. doi: 10.1021/ol802892h.

Enantioselective organocatalytic michael addition of malonates to alpha,beta-unsaturated ketones.

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1
Dalian Institute of Chemical Physics, Chinese Academy of Science, 457 Zhongshan Road, Dalian 116023, P. R. China.

Abstract

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.

PMID:
19115980
DOI:
10.1021/ol802892h
[Indexed for MEDLINE]
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