REGIOSELECTIVE AND STEREOSELECTIVE RING-OPENING OF 2,3-EPOXYALCOHOLS WITH DIETHYLALUMINUM AZIDE

Authors
BENEDETTI F BERTI F NORBEDO S
Citation
F. Benedetti et al., REGIOSELECTIVE AND STEREOSELECTIVE RING-OPENING OF 2,3-EPOXYALCOHOLS WITH DIETHYLALUMINUM AZIDE, Tetrahedron letters, 39(43), 1998, pp. 7971-7974
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
43
Year of publication
1998
Pages
7971 - 7974
Database
ISI
SICI code
0040-4039(1998)39:43<7971:RASRO2>2.0.ZU;2-M
Abstract
2,3-Epoxyalcohols react with diethylaluminium azide under mild conditi ons to give 3-azido-1,2-diols resulting from the regio- and stereosele ctive attack of the nucleophile at the epoxide C-3. The high regiosele ctivity (>25:1) observed with both cis and trans substituted epoxides is not affected by bulky substituents at C-3. The method has been succ essfully applied also to the synthesis of diaminodiol dipeptide isoste res, (C) 1998 Elsevier Science Ltd. All rights reserved.