ASYMMETRIC-SYNTHESIS OF BICYCLO[4.3.0]NONAN-8-ONES BY INTRAMOLECULAR PAUSON-KHAND REACTION

Authors
CASTRO J MOYANO A PERICAS MA RIERA A GREENE AE
Citation
J. Castro et al., ASYMMETRIC-SYNTHESIS OF BICYCLO[4.3.0]NONAN-8-ONES BY INTRAMOLECULAR PAUSON-KHAND REACTION, Tetrahedron : asymmetry, 5(3), 1994, pp. 307-310
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
3
Year of publication
1994
Pages
307 - 310
Database
ISI
SICI code
0957-4166(1994)5:3<307:AOBBIP>2.0.ZU;2-L
Abstract
The intramolecular Pauson-Khand reaction of (E)-1-alkoxy-1-octen-7-yne s derived from (1S,2R)-2-phenylcyclohexanol is described. 7-Alkoxybicy clo[4.3.0]non-1(9)-en-8-ones are obtained in yields up to 65% and with diastereoselectivities higher than 10:1. The absolute configuration o f the major diastereomer obtained has been ascertained and can be rati onalized on the basis of the preferential conformation of the precurso r.