Zirconium cation coordination in the borohydride-mediated synthesis of beta-hydroxy-N-alkoxylamines

Authors
Williams, DR Benbow, JW Sattleberg, TR Ihle, DC
Citation
Dr. Williams et al., Zirconium cation coordination in the borohydride-mediated synthesis of beta-hydroxy-N-alkoxylamines, TETRAHEDR L, 42(49), 2001, pp. 8597-8601
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
49
Year of publication
2001
Pages
8597 - 8601
Database
ISI
SICI code
0040-4039(200112)42:49<8597:ZCCITB>2.0.ZU;2-6
Abstract
Hydride reductions of oxime ethers to hydroxylamine derivatives are facilit ated by the participation of neighboring hydroxyl groups. Precomplexation w ith zirconium cation in ether-methylene chloride solutions is effective for selective C=N bond reduction. The course for stereochemical control is dic tated by Lewis acid coordination complexes of E- and Z-oximino ethers which lead to the preferred diastereofacial delivery of external hydride. (C) 20 01 Elsevier Science Ltd. All rights reserved.