An enantioselective synthesis of nitrogen protected 3-arylserine esters

…, DJ Fairfax, GS Martin, CJ Mathison, P Zhichkin

Index: Bourdon, Lisa H.; Fairfax, David J.; Martin, Gregory S.; Mathison, Casey J.; Zhichkin, Pavel Tetrahedron Asymmetry, 2004 , vol. 15, # 22 p. 3485 - 3487

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Citation Number: 15

Abstract

A method for the preparation of (2R, 3S) nitrogen protected arylserine esters is described. The method consists of rhodium mediated insertion of tert-butylcarbamate into the corresponding 3-keto-2-diazoester, affording the N-protected α-amino-β-ketoester, followed by asymmetric reduction/dynamic resolution to afford the corresponding N-protected 3- arylserine esters in good chemical yield, and in most cases high enantiomeric excess.

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