Oxidative cyclization of 1,4-dienes to yield 2,3,5-trisubstituted tetrahydrofuran-diols

Authors
Travis, B Borhan, B
Citation
B. Travis et B. Borhan, Oxidative cyclization of 1,4-dienes to yield 2,3,5-trisubstituted tetrahydrofuran-diols, TETRAHEDR L, 42(44), 2001, pp. 7741-7745
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
44
Year of publication
2001
Pages
7741 - 7745
Database
ISI
SICI code
0040-4039(20011029)42:44<7741:OCO1TY>2.0.ZU;2-1
Abstract
KMnO4 and OsO4 catalyze the oxidative cyclization of 1,4-dienes to provide 2,3,5-trisubstituted tetra hydrofuran-diols in 30%, yield. This reaction pr oceeds stereoselectively via a proposed [3+2] cycloaddition. Competing oxid ative pathways are the major non-productive processes that reduce the yield of the reaction, however, four stereogenic centers are established in one- step. (C) 2001 Elsevier Science Ltd. All rights reserved.