Cerium(III) chloride promoted opening of [3.2.1] oxabicycles with methyllithium

Authors
Lautens, M de Frutos, O Stammers, TA
Citation
M. Lautens et al., Cerium(III) chloride promoted opening of [3.2.1] oxabicycles with methyllithium, TETRAHEDR L, 40(48), 1999, pp. 8317-8321
Citations number
33
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
48
Year of publication
1999
Pages
8317 - 8321
Database
ISI
SICI code
0040-4039(19991126)40:48<8317:CCPOO[>2.0.ZU;2-S
Abstract
Previously reported 1-cyclohexylhydroxymethyl-2,4-dimethyl-8-oxabicyclo [3. 2.1]octen-3-ols 2 can be ring opened to produce substituted cycloheptenes 3 in a highly regio- and stereoselective reaction using MeLi in the presence of CeCl3. These functionalized cycloheptenes contain an array of five cont iguous stereocenters which provide access to polypropionate fragments with 1,3,5-syn,syn methyl groups. (C) 1999 Elsevier Science Ltd. All rights rese rved.