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Organocatalytic Asymmetric Sulfa‐Michael Additions to α,β‐Unsaturated Sulfonates
Author(s) -
Enders Dieter,
Hoffman Krzysztof
Publication year - 2009
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.200801202
Subject(s) - michael reaction , chemistry , bifunctional , thiourea , organocatalysis , reactivity (psychology) , catalysis , organic chemistry , enantioselective synthesis , adduct , addition reaction , asymmetric induction , medicinal chemistry , medicine , alternative medicine , pathology
The reactivity of α,β‐unsaturated sulfonates and aromaticthiols in an organocatalyzed sulfa‐Michael addition was explored. Bifunctional chiral thiourea catalysts were found to promote the reaction, and the corresponding Michael adducts were afforded in moderate to good yields (24–92 %) and with moderate levels of asymmetric induction (33–64 % ee ). This study represents the first use of α,β‐unsaturated sulfonates in a catalytic asymmetric Michael addition. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)