Issue 64, 2012
From the journal:

Chemical Communications

Catalytic asymmetric Mannich-type reactions of α-cyano α-sulfonyl carbanions†‡

Kohsuke Ohmatsu,a   Ayano Gotoa  and  Takashi Ooi*a  

* Corresponding authors

a Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Nagoya, Japan
E-mail: tooi@apchem.nagoya-u.ac.jp
Fax: +81 52 789 3338
Tel: +81 52 789 4501

Abstract

An efficient asymmetric Mannich-type reaction of α-cyano α-sulfonyl carbanions has been achieved by exploiting the structural modularity and anion-recognition ability of chiral 1,2,3-triazolium ions. This protocol has proven to be applicable to a variety of N-Boc imines and cyanosulfones, affording β-amino α-cyanosulfones in excellent yields with high stereoselectivities.

Graphical abstract: Catalytic asymmetric Mannich-type reactions of α-cyano α-sulfonyl carbanions

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Article information

DOI
https://doi.org/10.1039/C2CC32398B
Article type
Communication
Submitted
03 Apr 2012
Accepted
16 May 2012
First published
16 May 2012

Chem. Commun., 2012,48, 7913-7915

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Catalytic asymmetric Mannich-type reactions of α-cyano α-sulfonyl carbanions

K. Ohmatsu, A. Goto and T. Ooi, Chem. Commun., 2012, 48, 7913 DOI: 10.1039/C2CC32398B

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