A highly stereoselective entry to alpha-hydroxy carboxylic acids using D-fructose diacetonide as a chiral auxiliary

Authors
Yu, HW Ballard, E Wang, BH
Citation
Hw. Yu et al., A highly stereoselective entry to alpha-hydroxy carboxylic acids using D-fructose diacetonide as a chiral auxiliary, TETRAHEDR L, 42(10), 2001, pp. 1835-1838
Citations number
48
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
10
Year of publication
2001
Pages
1835 - 1838
Database
ISI
SICI code
0040-4039(20010304)42:10<1835:AHSETA>2.0.ZU;2-W
Abstract
Protected alpha -hydroxy carboxylic acids were synthesized in moderate yiel d and high diastereoselectivity by alkylation of glycolate ester enolates u sing a D-fructose-derived chiral auxiliary. The new chiral center was assig ned the (R)-configuration based upon comparisons to the literature. Both en antiomers of the auxiliary are readily available. (C) 2001 Published by Els evier Science Ltd.