Asymmetric nucleophilic α-amino-acylation with metalated chiral amino nitriles: enantioselective synthesis of 3-substituted 5-amino-4-oxo-esters via asymmetric …

D Enders, JP Shilvock, G Raabe

Index: Enders, Dieter; Shilvock, John P.; Raabe, Gerhard Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 12 p. 1617 - 1619

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Citation Number: 2

Abstract

Highly stereoselective conjugate addition of an enantio-pure metalated β-amino substituted amino nitrile to α, β-unsaturated esters, with subsequent silver nitrate induced hydrolysis of the amino nitrile adducts affords 3-substituted 5-amino-4-oxo-esters with high enantiomeric purity, thus achieving the overall asymmetric Michael addition of an α-amino-acyl carbanion.

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