REGIOSELECTIVE AND STEREOSELECTIVE REDUCTIVE CLEAVAGE OF 1,7-DIOXASPIRO[5.5]UNDECANE ALCOHOLS

Authors
CRIMMINS MT RAFFERTY SW
Citation
Mt. Crimmins et Sw. Rafferty, REGIOSELECTIVE AND STEREOSELECTIVE REDUCTIVE CLEAVAGE OF 1,7-DIOXASPIRO[5.5]UNDECANE ALCOHOLS, Tetrahedron letters, 37(32), 1996, pp. 5649-5652
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
32
Year of publication
1996
Pages
5649 - 5652
Database
ISI
SICI code
0040-4039(1996)37:32<5649:RASRCO>2.0.ZU;2-R
Abstract
Lewis acid-promoted triethylsilane reduction of 6,6-spiroketol alcohol s produces cis-2,6-disubstituted tetrahydropyrans with excellent regio selectivity and stereocontrol. An appended alcohol allows bidentate co ordination of the Lewis acid to selectively activate one CO bond of th e anomeric center toward reductive cleavage. Copyright (C) 1996 Elsevi er Science Ltd