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

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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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Article Details

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

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