Christophe Grosjean - The first example of enamine–Lewis acid cooperative bifunctional catalysis: application to the asymmetric Aldol reaction

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  Publication Details (including relevant citation   information): Arnold, K.; Batsanov, A. S.; Davies, B.;   Grosjean, C.; Schuetz, T.; Whiting, A.; Zawatzky, K. Chem.   Commun., 2008, 3879‐3881

  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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