Optically active sugar thioamides from delta-gluconolactone

Authors
Arevalo, MJ Avalos, M Babiano, R Cabanillas, A Cintas, P Jimenez, JL Palacios, JC
Citation
Mj. Arevalo et al., Optically active sugar thioamides from delta-gluconolactone, TETRAHEDR-A, 11(9), 2000, pp. 1985-1995
Citations number
36
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
9
Year of publication
2000
Pages
1985 - 1995
Database
ISI
SICI code
0957-4166(20000519)11:9<1985:OASTFD>2.0.ZU;2-G
Abstract
This paper describes a facile and rapid approach to N-alkyl- and N-aryl-thi ogluconamides employing delta-gluconolactone as starting material. The prot ocol involves a three-step sequence to afford the corresponding thioamides as crystalline substances in moderate to good yields. The Lawesson reagent was found to be the reagent of choice to accomplish the key transformation amide-thioamide. (C) 2000 Elsevier Science Ltd. All rights reserved.