Issue 90, 2013

Enantioselective synthesis of α-nitro-δ-ketosulfones via a quinine–squaramide catalyzed conjugate addition of α-nitrosulfones to enones

Abstract

Conjugate addition of α-nitrosulfones to vinyl ketones in the presence of 0.2 mol% of a quinine–squaramide organocatalyst afforded α-nitro-δ-ketosulfones possessing a tetrasubstituted chiral center in excellent yield and enantioselectivity in most cases. This strategy also offers a facile and convenient entry into γ-sulfonylhydroxamates that are one carbon homologs of potent enzyme inhibitors.

Graphical abstract: Enantioselective synthesis of α-nitro-δ-ketosulfones via a quinine–squaramide catalyzed conjugate addition of α-nitrosulfones to enones

Supplementary files

Article information

Article type
Communication
Submitted
05 Aug 2013
Accepted
25 Sep 2013
First published
26 Sep 2013
This article is Open Access
Creative Commons BY license

Chem. Commun., 2013,49, 10632-10634

Enantioselective synthesis of α-nitro-δ-ketosulfones via a quinine–squaramide catalyzed conjugate addition of α-nitrosulfones to enones

K. Bera and I. N. N. Namboothiri, Chem. Commun., 2013, 49, 10632 DOI: 10.1039/C3CC45985C

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