Base Free Catalyzed Enantioselective Michael Reaction of bis(phenylsulfonyl)methane to α,β -Unsaturated Aldehydes under Iminium Activation

Author(s): Beatriz Alonso, Uxue Uria, Luisa Carrillo, Jose L. Vicario, Efraim Reyes.

Journal Name: Current Topics in Medicinal Chemistry

Volume 14 , Issue 10 , 2014

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Abstract:

The Michael reaction of bis(phenylsulfonyl)methane with α,β-unsaturated aldehydes in the presence of catalytic amounts of a chiral secondary amine is presented. This transformation proceeds in good to excellent yields furnishing the corresponding Michael adducts in excellent enantioselectivities. Furthermore, other chiral building blocks are accessible from the obtained adducts by carrying out selective manipulation of the functional groups present at their structure, being possible to obtain a wide variety of sulfones with good results.

Keywords: Aldehydes, aminocatalysis, Michael addition, organocatalysis, sulfones.

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Article Details

VOLUME: 14
ISSUE: 10
Year: 2014
Page: [1317 - 1322]
Pages: 6
DOI: 10.2174/1568026614666140423114516
Price: $58

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