Issue 23, 2010
From the journal:

Chemical Communications

Asymmetric addition of α-hetero-disubstituted aldehydes to vinyl sulfones; formation of highly functionalized tetrasubstituted carbon centres†

Adrien Quintarda  and  Alexandre Alexakis*a  

* Corresponding authors

a Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet, 30, 1211, Geneva 4, Switzerland
E-mail: alexandre.alexakis@unige.ch
Tel: 0041 (0)22 379 65 22

Abstract

Aminal–pyrrolidine catalysed addition of α-hetero-disubstituted aldehydes to vinyl sulfones is described in high enantioselectivity (ee up to 97%). The obtained adducts can easily be converted to enantioenriched synthons as for example 2,2-dialkylepoxide. Evidence for a kinetic resolution is also observed.

Graphical abstract: Asymmetric addition of α-hetero-disubstituted aldehydes to vinyl sulfones; formation of highly functionalized tetrasubstituted carbon centres

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Article information

DOI
https://doi.org/10.1039/C000326C
Article type
Communication
Submitted
06 Jan 2010
Accepted
26 Mar 2010
First published
16 Apr 2010

Chem. Commun., 2010,46, 4085-4087

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Asymmetric addition of α-hetero-disubstituted aldehydes to vinyl sulfones; formation of highly functionalized tetrasubstituted carbon centres

A. Quintard and A. Alexakis, Chem. Commun., 2010, 46, 4085 DOI: 10.1039/C000326C

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