STUDIES ON THE CHEMOSELECTIVITY AND DIASTEREOSELECTIVITY OF SAMARIUM(II) IODIDE MEDIATED TRANSFORMATIONS OF CARBOHYDRATE-DERIVED OMEGA-HALO-ALPHA,BETA-UNSATURATED ESTERS

Authors
BENNETT SM BIBOUTOU RK ZHOU ZH PION R
Citation
Sm. Bennett et al., STUDIES ON THE CHEMOSELECTIVITY AND DIASTEREOSELECTIVITY OF SAMARIUM(II) IODIDE MEDIATED TRANSFORMATIONS OF CARBOHYDRATE-DERIVED OMEGA-HALO-ALPHA,BETA-UNSATURATED ESTERS, Tetrahedron, 54(19), 1998, pp. 4761-4786
Citations number
52
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
19
Year of publication
1998
Pages
4761 - 4786
Database
ISI
SICI code
0040-4020(1998)54:19<4761:SOTCAD>2.0.ZU;2-E
Abstract
Some carbohydrate derived omega-bromo- and omega-iodo- alpha,beta-unsa turated esters were reduced with SmI2 under a variety of conditions. T he chemoselectivity varies dramatically with the choice of solvent sys tem, the identity of halogen atom, the type of ester used, the geometr y of the double bond, and the oxygenation pattern of the substrate. Th e stereoselectivity of the SmI2 mediated reactions is also influenced by the reaction parameters. (C) 1998 Elsevier Science Ltd. All rights reserved.