Issue 11, 2006

Direct enantio- and diastereoselective Mannich reactions of malonate and β-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative

Abstract

A highly enantioselective Mannich reaction between malonate esters and N-Boc and N-Cbz aldimines, catalysed by a bifunctional cinchonine derivative, has been developed; extension of this methodology to encompass the use of 2-substituted-1,3-dicarbonyl nucleophiles allows the formation of adjacent stereocentres, one of which is quaternary, in high relative and absolute stereocontrol.

Graphical abstract: Direct enantio- and diastereoselective Mannich reactions of malonate and β-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative

Supplementary files

Article information

Article type
Communication
Submitted
04 Nov 2005
Accepted
20 Dec 2005
First published
01 Feb 2006

Chem. Commun., 2006, 1191-1193

Direct enantio- and diastereoselective Mannich reactions of malonate and β-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative

A. L. Tillman, J. Ye and D. J. Dixon, Chem. Commun., 2006, 1191 DOI: 10.1039/B515725K

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