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Influence of the Reaction Conditions on the Evolution of the Michael Addition of β‐Keto Sulfones to α,β‐Unsaturated Aldehydes
Author(s) -
Alemán José,
Marcos Vanesa,
Marzo Leyre,
García Ruano José Luis
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000502
Subject(s) - chemistry , michael reaction , silylation , adduct , conjugated system , organic chemistry , tandem , addition reaction , organocatalysis , reaction conditions , catalysis , enantioselective synthesis , polymer , materials science , composite material
We have studied the influence of different reaction conditions on the conjugated addition of β‐keto sulfones to α,β‐unsaturated aldehydes catalyzed by silyl prolinol ethers. Small changes in the starting material and/or in the experimental protocol are able to produce significant variations in the structures of the final products. The high chemical versatility of the resulting Michael adducts make possible their use in a variety of tandem and one‐pot reactions to afford polysubstituted cyclic products bearing multiple chiral centers.