The first example of enamine-Lewis acid cooperative bifunctional catalysis: application to the asymmetric aldol reaction |
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Authors: | Arnold Kenny Batsanov Andrei S Davies Bryan Grosjean Christophe Schütz Thorben Whiting Andrew Zawatzky Kerstin |
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Institution: | Department of Chemistry, Science Laboratories, Durham University, South Road, Durham, UK. |
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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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