Stereoselective synthesis of syn-alpha-methyl-beta-hydroxy esters

Authors
Carda, M Murga, J Falomir, E Gonzalez, F Marco, JA
Citation
M. Carda et al., Stereoselective synthesis of syn-alpha-methyl-beta-hydroxy esters, TETRAHEDR-A, 11(15), 2000, pp. 3211-3220
Citations number
49
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
15
Year of publication
2000
Pages
3211 - 3220
Database
ISI
SICI code
0957-4166(20000811)11:15<3211:SSOSE>2.0.ZU;2-0
Abstract
Boron enolates of an ethyl ketone structurally related to erythrulose react with achiral aldehydes in a highly stereoselective fashion to yield 1,2-sq n/1,3-syn stereoisomers. Oxidative cleavage of the aldol adducts yields ena ntiopure O-formylated syn-alpha-methyl-beta-hydroxy eaters, easily cleaved to the corresponding hydroxyl-free compounds. The aforementioned ketone beh aves therefore as a chiral propionate enolate equivalent. (C) 2000 Elsevier Science Ltd. All rights reserved.