Homoallylic alcohols and trichloroacetamides as hydrogen bond donors for directed dihydroxylation

Authors
Donohoe, TJ Mitchell, L Waring, MJ Helliwell, M Bell, A Newcombe, NJ
Citation
Tj. Donohoe et al., Homoallylic alcohols and trichloroacetamides as hydrogen bond donors for directed dihydroxylation, TETRAHEDR L, 42(51), 2001, pp. 8951-8954
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
51
Year of publication
2001
Pages
8951 - 8954
Database
ISI
SICI code
0040-4039(200112)42:51<8951:HAATAH>2.0.ZU;2-0
Abstract
The synthesis and directed dihydroxylation of a series of homoallylic alcoh ols and trichloroacetamides is described. Using the combination of OsO4 and TMEDA, moderate to high levels of stereoselectivity were obtained, dependi ng upon the structure of the substrate. Proof of the structure of two osmat e esters was obtained through X-ray crystallography. (C) 2001 Elsevier Scie nce Ltd. All rights reserved.