A SIMPLE PROCEDURE FOR THE PREPARATION OF ENANTIOPURE ETHYL ALPHA-HYDROXYALKYL KETONES

Authors
MARTIN R PASCUAL O ROMEA P ROVIRA R URPI F VILARRASA J
Citation
R. Martin et al., A SIMPLE PROCEDURE FOR THE PREPARATION OF ENANTIOPURE ETHYL ALPHA-HYDROXYALKYL KETONES, Tetrahedron letters, 38(9), 1997, pp. 1633-1636
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
9
Year of publication
1997
Pages
1633 - 1636
Database
ISI
SICI code
0040-4039(1997)38:9<1633:ASPFTP>2.0.ZU;2-Z
Abstract
Amides derived from pyrrolidine and methyl (S)-lactate, methyl (S)-2-h ydroxy-3-phenylpropanoate, or methyl (S)-2-hydroxy-3-methylbutanoate, after O-benzylation and O-silylation have been treated with EtLi or Et MgCl under suitable conditions, to give excellent overall yields of en antiopure ethyl ketones. The chelating ability of alpha-OBn amides (an d even of alpha-O-TBS amides, which has been demonstrated by NMR to be better than that of N-OMe amides) accounts for the performance of the approach. (C) 1997 Elsevier Science Ltd.