HIGHLY REGIOSELECTIVE NUCLEOPHILIC-SUBSTITUTION OF CYCLIC CARBONATES OF THREO-2,3-DIHYDROXY ESTERS - SYNTHESIS OF OPTICALLY PURE BETA-HYDROXY ESTERS

Authors
KANG SK PARK DC RHO HS YOON SH SHIN JS
Citation
Sk. Kang et al., HIGHLY REGIOSELECTIVE NUCLEOPHILIC-SUBSTITUTION OF CYCLIC CARBONATES OF THREO-2,3-DIHYDROXY ESTERS - SYNTHESIS OF OPTICALLY PURE BETA-HYDROXY ESTERS, Journal of the Chemical Society. Perkin transactions. I, (24), 1994, pp. 3513-3514
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
24
Year of publication
1994
Pages
3513 - 3514
Database
ISI
SICI code
0300-922X(1994):24<3513:HRNOCC>2.0.ZU;2-W
Abstract
The nucleophilic ring opening of the cyclic carbonates of optically ac tive threo-2,3-dihydroxy eaters 1 afforded the alpha-substituted beta- hydroxy esters 2 with highly regio- and stereo-selectivity under mild conditions. The alpha-sulfanyl or alpha-iodo beta-hydroxy esters 2 thu s obtained were transformed to the beta-hydroxy esters 3, which are us eful chiral synthons' for natural product synthesis.