ASYMMETRIC REACTIONS OF ALPHA-KETOACID-DERIVED HEMIACETALS - STEREOSELECTIVE SYNTHESIS OF ALPHA-HYDROXY ACIDS

Authors
PANSARE SV RAVI RG
Citation
Sv. Pansare et Rg. Ravi, ASYMMETRIC REACTIONS OF ALPHA-KETOACID-DERIVED HEMIACETALS - STEREOSELECTIVE SYNTHESIS OF ALPHA-HYDROXY ACIDS, Tetrahedron, 54(48), 1998, pp. 14549-14564
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
48
Year of publication
1998
Pages
14549 - 14564
Database
ISI
SICI code
0040-4020(1998)54:48<14549:AROAH->2.0.ZU;2-O
Abstract
N-Acylation of prolinol with alpha-ketoacid chlorides results in conco mitant hemiacetalization of the alpha-keto amide by the prolinol hydro xyl group, (R) or (S) alpha-hydroxy acids are obtained with good enant iomeric excess by stereodivergent reduction of these hemiacetals. Reac tion with Grignard reagents at ambient temperature furnishes (R) alpha -alkyl mandelic acids with good stereoselectivity. (C) 1998 Elsevier S cience Ltd. All rights reserved.