CHIRALITY PRESERVATION OF A CATION-RADICAL INTERMEDIATE - TANDEM OXIDATIVE RING EXPANSION-CYCLIZATION REACTION OF OPTICALLY-ACTIVE BICYCLO[4.1.0]HEPTYL SULFIDES

Authors
TAKEMOTO Y OHRA T KOIKE H FURUSE S IWATA C OHISHI H
Citation
Y. Takemoto et al., CHIRALITY PRESERVATION OF A CATION-RADICAL INTERMEDIATE - TANDEM OXIDATIVE RING EXPANSION-CYCLIZATION REACTION OF OPTICALLY-ACTIVE BICYCLO[4.1.0]HEPTYL SULFIDES, Journal of organic chemistry, 59(17), 1994, pp. 4727-4729
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
17
Year of publication
1994
Pages
4727 - 4729
Database
ISI
SICI code
0022-3263(1994)59:17<4727:CPOACI>2.0.ZU;2-M
Abstract
Asymmetric synthesis of 1-oxaspiro[4.6]undecan-7-one and spiro[4.6]und ecanes has been achieved by a regio- and stereoselective tandem oxidat ive ring expansion-cyclization reaction of chiral bicyclo[4.1.0]heptyl sulfides bearing an alcohol or electron-rich olefin in the C-6 side c hain via a cation radical intermediate.