Article

Organocatalytic asymmetric Michael-type/Wittig reaction of phosphorus ylides: synthesis of chiral α-methylene-δ-ketoesters.

School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, China.
Organic Letters (impact factor: 5.86). 08/2011; 13(16):4176-9. DOI:10.1021/ol201483s pp.4176-9
Source: PubMed

ABSTRACT An asymmetric Michael-type reaction of phosphorus ylides and α,β-unsaturated ketones under the catalysis of a chiral ion pair catalyst has been described. The ion pair catalyst containing a chiral counteranion was prepared by simply mixing 9-amino-(9-deoxy)-epi-quinine with l-N-Boc-proline. The optically active α-methylene-δ-ketoesters could be obtained with good to excellent enantioselectivities (up to 95% ee) under mild reaction conditions.

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Keywords

9-amino-(9-deoxy)-epi-quinine
 
asymmetric Michael-type reaction
 
chiral counteranion
 
chiral ion pair catalyst
 
excellent enantioselectivities
 
ion pair catalyst
 
optically active α-methylene-δ-ketoesters
 

Aijun Lin