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

(-)-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 especia...

Full description

Saved in:
Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2008-01 (33), p.3879-3881
Main Authors: Arnold, Kenny, Batsanov, Andrei S, Davies, Bryan, Grosjean, Christophe, Schütz, Thorben, Whiting, Andrew, Zawatzky, Kerstin
Format: Article
Language:English
Subjects:
Acids - chemistry
Aldehydes - chemistry
Amines - chemistry
Catalysis
Lewis Acids - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:(-)-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.
ISSN:1359-7345
1364-548X
DOI:10.1039/b806779a