An efficient method to chiral beta-hydroxy acids: Synthesis of lipid-A side chain

Authors
Nandanan, E Phukan, P Sudalai, A
Citation
E. Nandanan et al., An efficient method to chiral beta-hydroxy acids: Synthesis of lipid-A side chain, I J CHEM B, 38(8), 1999, pp. 893-896
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
ISSN journal
03764699 → ACNP
Volume
38
Issue
8
Year of publication
1999
Pages
893 - 896
Database
ISI
SICI code
0376-4699(199908)38:8<893:AEMTCB>2.0.ZU;2-R
Abstract
The synthesis of optically active beta-hydroxy acids 5a-c is achieved in fo ur steps from their corresponding terminal olefins 1a-c by employing Sharpl ess asymmetric dihydroxylation. The regioselective ring opening of chiral c yclic sulfites 3a-c with cyanide ion, constitutes the key reaction, thus pr oducing the hydroxy nitriles 4a-c.