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

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

Journal Name: Letters in Organic Chemistry

Volume 6 , Issue 8 , 2009

Become EABM
Become Reviewer

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

Rights & PermissionsPrintExport Cite as


Article Details

VOLUME: 6
ISSUE: 8
Year: 2009
Page: [593 - 597]
Pages: 5
DOI: 10.2174/157017809790443014
Price: $58

Article Metrics

PDF: 1