EFFICIENT DIASTEREOSELECTIVE SYNTHESIS OF ALPHA,BETA-DIHYDROXYESTERS FROM METHYL PHENYLGLYOXYLATE AND ALDEHYDES MEDIATED BY TITANIUM TRICHLORIDE PYRIDINE SYSTEM/

Authors
CLERICI A CLERICI L MALPEZZI L PORTA O
Citation
A. Clerici et al., EFFICIENT DIASTEREOSELECTIVE SYNTHESIS OF ALPHA,BETA-DIHYDROXYESTERS FROM METHYL PHENYLGLYOXYLATE AND ALDEHYDES MEDIATED BY TITANIUM TRICHLORIDE PYRIDINE SYSTEM/, Tetrahedron, 51(48), 1995, pp. 13385-13400
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
48
Year of publication
1995
Pages
13385 - 13400
Database
ISI
SICI code
0040-4020(1995)51:48<13385:EDSOAF>2.0.ZU;2-L
Abstract
The reductive coupling of methyl phenylglyoxylate 2 with aliphatic and aromatic aldehydes 3, promoted by TiCl3/Py system in anhydrous THF, a ffords alpha,beta-dihydroxyesters 4 in good yields (60-94%) and high s yn-diastereoselectivity (up to 85%). The type of ligand at the metal i on necessary to achieve a high level of diastereocontrol and the possi ble mechanism involved are discussed.