ASYMMETRIC-SYNTHESIS OF HOMOCHIRAL 1,2-DIOLS VIA N-BOC OXAZOLIDINES

Authors
AGAMI C COUTY F LEQUESNE C
Citation
C. Agami et al., ASYMMETRIC-SYNTHESIS OF HOMOCHIRAL 1,2-DIOLS VIA N-BOC OXAZOLIDINES, Tetrahedron letters, 35(20), 1994, pp. 3309-3312
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
20
Year of publication
1994
Pages
3309 - 3312
Database
ISI
SICI code
0040-4039(1994)35:20<3309:AOH1VN>2.0.ZU;2-0
Abstract
Diastereoisomerically pure N-Boc 2-acyloxazolidines were synthesized f rom phenylglyoxal and ethyl glyoxylate. Reaction of these heterocycles with Grignard reagents is highly stereoselective. Homochiral 1,2-diol s were ultimately obtained after N-deprotection, hydrolysis and reduct ion of the intermediate alpha-hydroxy aldehyde. The asymmetric inducti on can be explained by a chelated model.