Issue 11, 2012
From the journal:

Chemical Science

Chiral ionic Brønsted acid–achiral Brønsted base synergistic catalysis for asymmetric sulfa-Michael addition to nitroolefins†

Daisuke Uraguchi,a   Natsuko Kinoshita,a   Daisuke Nakashimaa  and  Takashi Ooi*a  

* Corresponding authors

a Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya, 464-8603, Japan
E-mail: tooi@apchem.nagoya-u.ac.jp
Fax: +81-(0)52-789-3338
Tel: +81-(0)52-789-4501

Abstract

A highly enantioselective sulfa-Michael addition to aromatic and aliphatic nitroolefins is achieved under the synergistic catalysis of chiral, ionic Brønsted acid homo-1b·HBArF and 2,6-lutidine. The potential utility of this new method is clearly demonstrated by its application to the syntheses of a novel, optically active taurine derivative and β-sultam.

Graphical abstract: Chiral ionic Brønsted acid–achiral Brønsted base synergistic catalysis for asymmetric sulfa-Michael addition to nitroolefins

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Article information

DOI
https://doi.org/10.1039/C2SC20698F
Article type
Edge Article
Submitted
31 May 2012
Accepted
06 Jul 2012
First published
06 Jul 2012

Chem. Sci., 2012,3, 3161-3164

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Chiral ionic Brønsted acid–achiral Brønsted base synergistic catalysis for asymmetric sulfa-Michael addition to nitroolefins

D. Uraguchi, N. Kinoshita, D. Nakashima and T. Ooi, Chem. Sci., 2012, 3, 3161 DOI: 10.1039/C2SC20698F

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