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Issue 33, 2008
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The first example of enamine–Lewis acid cooperative bifunctional catalysis: application to the asymmetric aldol reaction

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Abstract

(−)-Sparteine directed lithiation of N-Boc-pyrrolidine, alkylation with chloromethylboronate pinacol ester and acid-based deprotection provides homoboroproline HX salt in 94% ee, which is then an efficient enamine-type pyrrolidine catalyst in an asymmetric aldol reaction when neutralised and especially when esterified in situ with a tartrate ester, for example, providing 90% ee of the aldol adduct derived from acetone and p-nitrobenzaldehyde.

Graphical abstract: The first example of enamine–Lewis acid cooperative bifunctional catalysis: application to the asymmetric aldol reaction

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Article information


Submitted
21 Apr 2008
Accepted
14 May 2008
First published
24 Jun 2008

Chem. Commun., 2008, 3879-3881
Article type
Communication

The first example of enamine–Lewis acid cooperative bifunctional catalysis: application to the asymmetric aldol reaction

K. Arnold, A. S. Batsanov, B. Davies, C. Grosjean, T. Schütz, A. Whiting and K. Zawatzky, Chem. Commun., 2008, 3879
DOI: 10.1039/B806779A

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