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Novel bifunctional sulfonamides catalyze an enantioselective conjugate addition.

ABSTRACT: A new bifunctional organocatalyst with a novel structural and functional motif has been developed. This bifunctional sulfonamide organocatalyst was used in the conjugate addition of 1,3-dicarbonyl compounds (13) to ?-nitrostyrenes (12). Yields up to 91% and enantiomeric excesses up to 79% were obtained in this reaction. This catalyst activates both 13 via its basic moiety and 12 through hydrogen bonding.

SUBMITTER: McGarraugh PG

PROVIDER: S-EPMC2659672 | biostudies-literature | 2009 Jan

REPOSITORIES: biostudies-literature

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Novel bifunctional sulfonamides catalyze an enantioselective conjugate addition.

McGarraugh Patrick G PG Brenner Stacey E SE

Tetrahedron 20090101 2

A new bifunctional organocatalyst with a novel structural and functional motif has been developed. This bifunctional sulfonamide organocatalyst was used in the conjugate addition of 1,3-dicarbonyl compounds (13) to β-nitrostyrenes (12). Yields up to 91% and enantiomeric excesses up to 79% were obtained in this reaction. This catalyst activates both 13 via its basic moiety and 12 through hydrogen bonding. ...[more]

PMID: 20066026

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