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

Literature Information

Publication Date 2008-06-24
DOI 10.1039/B806779A
Impact Factor 6.222
Authors

Kenny Arnold, Andrei S. Batsanov, Bryan Davies, Christophe Grosjean, Thorben Schütz, Andrew Whiting, Kerstin Zawatzky


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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.

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