Stereoselective synthesis of oxazolidines from 2-amino-2-deoxy-D-allose derivatives and their reactivity with nucleophiles

Authors
Vega-Perez, JM Vega, M Blanco, E Iglesias-Guerra, F
Citation
Jm. Vega-perez et al., Stereoselective synthesis of oxazolidines from 2-amino-2-deoxy-D-allose derivatives and their reactivity with nucleophiles, TETRAHEDR-A, 12(1), 2001, pp. 135-147
Citations number
31
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
1
Year of publication
2001
Pages
135 - 147
Database
ISI
SICI code
0957-4166(20010205)12:1<135:SSOOF2>2.0.ZU;2-W
Abstract
The use of 2-amino-2-deoxy-D-allose in the synthesis of oxazolidines is des cribed. The reaction takes place with total stereoselectivity in the prepar ation of both simple oxazolidines (from aldehydes as reagent) and bicyclic oxazolidines (from chlorocarbonyl compounds and keto-acids as reagents). Th e reactivity of the obtained oxazolidines with hydride and alkylmagnesium c hlorides is also described. (C) 2001 Published by Elsevier Science Ltd. All rights reserved.