Issue 35, 2012
From the journal:

Organic & Biomolecular Chemistry

Chiral-Sc catalyzed asymmetric Michael addition/protonation of thiols with enones in water†

Taku Kitanosono,a   Masaru Sakai,a   Masaharu Uenoa  and  Shū Kobayashi*a  

* Corresponding authors

a Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, Japan
E-mail: shu_kobayashi@chem.s.u-tokyo.ac.jp
Fax: (+81)-3-5684-0634
Tel: (+81)-03-5841-4790

Abstract

Asymmetric Michael reactions and enantioselective protonations between enones and thiols were catalyzed by a Sc(OTf)3–chiral 2,2′-bipyridine complex in water. The remarkable governing of the enantioselectivity for simple introduction of protons despite their abnormally high mobility in water may provide us with new synthetic opportunities as well as significant chemical advances.

Graphical abstract: Chiral-Sc catalyzed asymmetric Michael addition/protonation of thiols with enones in water

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Article information

DOI
https://doi.org/10.1039/C2OB26264A
Article type
Paper
Submitted
11 Jun 2012
Accepted
06 Jul 2012
First published
06 Jul 2012

Org. Biomol. Chem., 2012,10, 7134-7147

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Chiral-Sc catalyzed asymmetric Michael addition/protonation of thiols with enones in water

T. Kitanosono, M. Sakai, M. Ueno and S. Kobayashi, Org. Biomol. Chem., 2012, 10, 7134 DOI: 10.1039/C2OB26264A

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