Stereoselectivity in the rhodium(II) acetate catalysed cyclopropanations of 2-diazo-1-indanone with styrenes

Authors
Bauta, W Dodd, J Bullington, J Gauthier, D Leo, G McDonnell, P
Citation
W. Bauta et al., Stereoselectivity in the rhodium(II) acetate catalysed cyclopropanations of 2-diazo-1-indanone with styrenes, TETRAHEDR L, 41(10), 2000, pp. 1491-1494
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
10
Year of publication
2000
Pages
1491 - 1494
Database
ISI
SICI code
0040-4039(20000304)41:10<1491:SITRAC>2.0.ZU;2-F
Abstract
The rhodium(II) acetate catalysed cyclopropanation reactions of 2-diazo-1-i ndanone 4 with various substituted styrenes 5 have been investigated. The c yclopropane diastereomer 6a bearing a trans relationship between the carbon yl and the aryl ring was in all cases the predominant isomer and the ratio of stereosiomers almost constant over a range of styrene substituents. Styr enes bearing electron-donating substituents gave slightly better stereosele ctivity in favour of the trans isomer, These results are substantiated by a mechanistic proposal. (C) 2000 Published by Elsevier Science Ltd. All righ ts reserved.