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Enantioselective Organocatalytic Michael Addition of α‐Substituted Cyanoacetates to α,β‐Unsaturated Selenones
Author(s) -
Marini Francesca,
Sternativo Silvia,
Del Verme Francesca,
Testaferri Lorenzo,
Tiecco Marcello
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800592
Subject(s) - enantioselective synthesis , stereocenter , chemistry , bifunctional , michael reaction , thiourea , organocatalysis , organic chemistry , adduct , addition reaction , urea , catalysis
A novel enantioselective (up to 90% ee ) Michael addition of α‐substituted cyanoacetates to α,β‐unsaturated selenones in the presence of bifunctional urea and thiourea organocatalysts is described. The Michael adducts, containing an all‐carbon quaternary stereocenter, are smoothly converted into synthetically useful polyfunctional compounds by taking advantage of the excellent leaving group ability of the selenone group.