A NEW GENERAL-METHOD TO OBTAIN CHIRAL 2-ALKYLGLYCIDIC ACID-DERIVATIVES - SYNTHESIS OF METHYL (R)-(-PALMOXIRATE())

Authors
RUANO JLG CASTRO AMM RODRIQUEZ JH
Citation
Jlg. Ruano et al., A NEW GENERAL-METHOD TO OBTAIN CHIRAL 2-ALKYLGLYCIDIC ACID-DERIVATIVES - SYNTHESIS OF METHYL (R)-(-PALMOXIRATE()), Journal of organic chemistry, 59(3), 1994, pp. 533-536
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
3
Year of publication
1994
Pages
533 - 536
Database
ISI
SICI code
0022-3263(1994)59:3<533:ANGTOC>2.0.ZU;2-N
Abstract
The hydrolysis of the diastereomerically pure cyanohydrins, obtained b y reaction of Et(2)AlCN with homochiral alpha-sulfinyl ketones, yielde d beta-sulfenyl esters or amides, which evolved into the corresponding 2-alkylglycidic acid derivatives tee >97%) by treatment with Me3O(+)B F(4)- and NaHCO3. The use of this sequence to synthesize optically pur e (R)-(+)-palmoxirate, a powerful hypoglicemic agent, is also describe d.