Enantioselective synthesis of alpha-hydroxy acids employing (1S)-(+)-N,N-diisopropyl-10-camphorsulfonamide as chiral auxiliary

Authors
Chang, JW Jang, DP Uang, BJ Liao, FL Wang, SL
Citation
Jw. Chang et al., Enantioselective synthesis of alpha-hydroxy acids employing (1S)-(+)-N,N-diisopropyl-10-camphorsulfonamide as chiral auxiliary, ORG LETT, 1(13), 1999, pp. 2061-2063
Citations number
34
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
13
Year of publication
1999
Pages
2061 - 2063
Database
ISI
SICI code
1523-7060(199912)1:13<2061:ESOAAE>2.0.ZU;2-1
Abstract
[GRAPHICS] Lewis acid (BF3. OEt2) catalyzed condensation of dimethoxy acetal 2 with al pha-hydroxy acids produces chiral 1,3-dioxolanones I. The enolates derived from these compounds undergo reactions with alkyl halides with a high level of diastereoselectivity. Subsequent hydrolysis of these alkylated products II gives mono- and disubstituted alpha-hydroxy acids III with high enantio meric excesses.