Chiral Squaramide‐Catalyzed Enantioselective Conjugate Michael Addition of Various Thiols to α,β‐Unsaturated  N ‐Acylated Oxazolidin‐2‐ones | Zendy

Dai Le | Zendy; Yang Hongjun | Zendy; Chen Fener | Zendy

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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.

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