A Diphenylprolinol TMS Ether/Bile Acid Organocatalytic System for the Asymmetric Domino Sulfa-Michael/Aldol Condensation Reactions of 1,4-Dithiane-2,5-diol and Cinnamaldehydes

Nikla      Baricordi; Simonetta      Benetti; Carmela      De Risi; Marco      Fogagnolo; Gian   Piero   Pollini; Vinicio      Zanirato

doi:10.2174/157017809790443014

Abstract

Organocatalytic asymmetric domino sulfa-Michael/aldol condensation reactions between 1,4-dithiane-2,5-diol (the dimer of mercaptoacetaldehyde) and cinnamaldehydes were efficiently promoted by (S)-diphenylprolinol TMS ether in the presence of bile acid derivatives, leading to hitherto unknown 4,5-dihydrothiophene-2-carbaldehydes in moderate to good yields and good enantioselectivities.

Keywords: Sulfa-Michael reactions, domino reactions, asymmetric organocatalysis, dihydrothiophenes, bile acids

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Letters in Organic Chemistry

Title: A Diphenylprolinol TMS Ether/Bile Acid Organocatalytic System for the Asymmetric Domino Sulfa-Michael/Aldol Condensation Reactions of 1,4-Dithiane-2,5-diol and Cinnamaldehydes

Volume: 6 Issue: 8

Author(s): Nikla Baricordi, Simonetta Benetti, Carmela De Risi, Marco Fogagnolo, Gian Piero Pollini and Vinicio Zanirato

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Keywords: Sulfa-Michael reactions, domino reactions, asymmetric organocatalysis, dihydrothiophenes, bile acids

Abstract: Organocatalytic asymmetric domino sulfa-Michael/aldol condensation reactions between 1,4-dithiane-2,5-diol (the dimer of mercaptoacetaldehyde) and cinnamaldehydes were efficiently promoted by (S)-diphenylprolinol TMS ether in the presence of bile acid derivatives, leading to hitherto unknown 4,5-dihydrothiophene-2-carbaldehydes in moderate to good yields and good enantioselectivities.

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Baricordi Nikla, Benetti Simonetta, De Risi Carmela, Fogagnolo Marco, Pollini Piero Gian and Zanirato Vinicio, A Diphenylprolinol TMS Ether/Bile Acid Organocatalytic System for the Asymmetric Domino Sulfa-Michael/Aldol Condensation Reactions of 1,4-Dithiane-2,5-diol and Cinnamaldehydes, Letters in Organic Chemistry 2009; 6 (8) . https://dx.doi.org/10.2174/157017809790443014