Issue 7, 2004
From the journal:

Chemical Communications

A catalytic and iterative route to β-substituted estersvia highly enantioselective conjugate addition of dimethylzinc to unsaturated malonates†

Julia Schuppan,a   Adriaan J. Minnaarda  and  Ben L. Feringa*a  

* Corresponding authors

a Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9749 AG Groningen, The Netherlands

Abstract

Using the chiral phosphoramidite ligand (S,R,R)-L1 in the conjugate addition of dimethylzinc to acyclic unsaturated malonates, enantioselectivities of up to 98% have been obtained for the first time. An iterative and stereodivergent route to 3,5-dimethyl esters that takes advantage of this asymmetric catalysis has been developed.

Graphical abstract: A catalytic and iterative route to β-substituted esters via highly enantioselective conjugate addition of dimethylzinc to unsaturated malonates

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Article information

DOI
https://doi.org/10.1039/B315871C
Article type
Communication
Submitted
05 Dec 2003
Accepted
28 Jan 2004
First published
24 Feb 2004

Chem. Commun., 2004, 792-793

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A catalytic and iterative route to β-substituted esters via highly enantioselective conjugate addition of dimethylzinc to unsaturated malonates

J. Schuppan, A. J. Minnaard and B. L. Feringa, Chem. Commun., 2004, 792 DOI: 10.1039/B315871C

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