Chemical communications

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

AL Tillman, J Ye, DJ Dixon

Index: Tillman, A. Louise; Ye, Jinxing; Dixon, Darren J. Chemical Communications, 2006 , # 11 p. 1191 - 1193

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Citation Number: 122

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.