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Chiral Squaramide‐Catalyzed Enantioselective Conjugate Michael Addition of Various Thiols to α,β‐Unsaturated N ‐Acylated Oxazolidin‐2‐ones
Author(s) -
Dai Le,
Yang Hongjun,
Chen Fener
Publication year - 2011
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.201100403
Subject(s) - squaramide , enantioselective synthesis , chemistry , michael reaction , conjugate , catalysis , adduct , thio , yield (engineering) , organic chemistry , organocatalysis , mathematical analysis , materials science , mathematics , metallurgy
A highly enantioselective sulfa‐Michael addition (SMA) of various thiols to α,β‐unsaturated N ‐acylated oxazolidinones has been achieved with a chiral squaramide catalyst under very mild reaction conditions. In addition, the conversion of the β‐thio‐substituted adduct to the corresponding methyl β‐tosylbutanoate was demonstrated in high yield through a methanolysis/oxidation sequence.