1.
J Org Chem
; 76(20): 8513-7, 2011 Oct 21.
Article
in English
| MEDLINE
| ID: mdl-21894973
ABSTRACT
Highly enantioselective Michael addition of malonates to enones was achieved using a mixed catalyst consisting of a primary ß-amino acid, O-TBDPS (S)-ß-homoserine, and its lithium salt. Various cyclic and acyclic enones were converted into 1,5-ketoesters in high yields (up to 92%) with high enantioselectivity (up to 97% ee) under mild reaction conditions. Details of synthesis of the catalyst, optimization of the reaction conditions for the Michael addition reaction, and a plausible reaction mechanism are described.