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Issue 11, 2006
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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

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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

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Publication details

The article was received on 04 Nov 2005, accepted on 20 Dec 2005 and first published on 01 Feb 2006


Article type: Communication
DOI: 10.1039/B515725K
Citation: Chem. Commun., 2006,0, 1191-1193
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    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, 0, 1191
    DOI: 10.1039/B515725K

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