Chiral primary amine mediated conjugate addition of branched aldehydes to vinyl sulfone: asymmetric generation of quaternary carbon centers

Qiang Zhu; Yixin Lu

doi:10.1039/B919549A

Chiral primary amine mediated conjugate addition of branched aldehydes to vinyl sulfone: asymmetric generation of quaternary carbon centers

Qiang Zhu^a^b and Yixin Lu*^a^b

* Corresponding authors

^a Department of Chemistry, National University of Singapore, Republic of Singapore
E-mail: chmlyx@nus.edu.sg
Fax: +65-6779-1691
Tel: +65-6516-1569

^b Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, Republic of Singapore

Abstract

Novel L-threonine-derived bifunctional organic catalysts containing primary amine and sulfonamide groups were utilized to promote asymmetric conjugate addition of α,α-disubstitued aldehydes to 1,1-bis(benzenesulfonyl)ethylene. The adducts with quaternary stereogenic centers adjacent to an aldehyde group were obtained in high yield and with good enantioselectivity.

Supplementary files

Publication details

The article was received on 18 Sep 2009, accepted on 22 Dec 2009 and first published on 21 Jan 2010

Article type: Communication

DOI: 10.1039/B919549A

Citation: Chem. Commun., 2010,46, 2235-2237

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Chiral primary amine mediated conjugate addition of branched aldehydes to vinyl sulfone: asymmetric generation of quaternary carbon centers

Q. Zhu and Y. Lu, Chem. Commun., 2010, 46, 2235
DOI: 10.1039/B919549A
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Chemical Communications

Chiral primary amine mediated conjugate addition of branched aldehydes to vinyl sulfone: asymmetric generation of quaternary carbon centers

Abstract

Supplementary files

Publication details

Chiral primary amine mediated conjugate addition of branched aldehydes to vinyl sulfone: asymmetric generation of quaternary carbon centers

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