title: The first example of enamine-Lewis acid cooperative bifunctional catalysis: application to the asymmetric aldol reaction.
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.
authors: Department of Chemistry, Science Laboratories, Durham University, South Road, Durham, UK.
authors: Kenny
authors: K
authors: Arnold
authors: Andrei S
authors: AS
authors: Batsanov
authors: Bryan
authors: B
authors: Davies
authors: Christophe
authors: C
authors: Grosjean
authors: Thorben
authors: T
authors: Schütz
authors: Andrew
authors: A
authors: Whiting
authors: Kerstin
authors: K
authors: Zawatzky
mesh_terms: D000143:Acids / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D058116:Lewis Acids / Q000737:chemistry*
chemical_list: D000143:Acids; D000447:Aldehydes; D000588:Amines; D058116:Lewis Acids; C116609:3-hydroxybutanal