Tetrahedron letters

A simple procedure for the preparation of enantiopure ethyl α-hydroxyalkyl ketones

…, O Pascual, P Romea, R Rovira, F Urpí, J Vilarrasa

Index: Martin, Ricardo; Pascual, Oscar; Romea, Pedro; Rovira, Roser; Urpi, Felix; Vilarrasa, Jaume Tetrahedron Letters, 1997 , vol. 38, # 9 p. 1633 - 1636

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Citation Number: 19

Abstract

Amides derived from pyrrolidine and methyl (S)-lactate, methyl (S)-2-hydroxy-3- phenylpropanoate, or methyl (S)-2-hydroxy-3-methylbutanoate, after O-benzylation and O- silylation have been treated with EtLi or EtMgCl under suitable conditions, to give excellent overall yields of enantiopure ethyl ketones. The chelating ability of α-OBn amides (and even of α-O-TBS amides, which has been demonstrated by NMR to be better than that of N- ...