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Enesulfonamides as Nucleophiles in Catalytic Asymmetric Reactions
Author(s) -
Matsubara Ryosuke,
Doko Takashi,
Uetake Ryosuke,
Kobayashi Shū
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200605054
Subject(s) - enantioselective synthesis , nucleophile , copper , catalysis , chemistry , combinatorial chemistry , product (mathematics) , sulfonamide , organic chemistry , mathematics , geometry
A biased copper‐coin toss : Highly diastereo‐ and enantioselective copper‐catalyzed addition reactions of enesulfonamides to α‐keto aldehydes and azodicarboxylates have been developed. Low loadings of the chiral copper catalyst efficiently promoted the reaction (see scheme). The product sulfonylimines could be reduced diastereoselectively to the biologically important chiral sulfonamide compounds.