CYCLOPENTA[B]INDOLES .1. SYNTHESIS OF CYCLOPENTA[B]INDOLES BY FORMAL [3+2] ADDITION OF INDOLYLMETHYL CATIONS TO ALKENES

Authors
HARRISON CA LEINEWEBER R MOODY CJ WILLIAMS JMJ
Citation
Ca. Harrison et al., CYCLOPENTA[B]INDOLES .1. SYNTHESIS OF CYCLOPENTA[B]INDOLES BY FORMAL [3+2] ADDITION OF INDOLYLMETHYL CATIONS TO ALKENES, Journal of the Chemical Society. Perkin transactions. I, (9), 1995, pp. 1127-1130
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
9
Year of publication
1995
Pages
1127 - 1130
Database
ISI
SICI code
0300-922X(1995):9<1127:C.SOCB>2.0.ZU;2-Z
Abstract
Treatment of indole-2- or 3-methanols with tin(rv) chloride as Lewis a cid in the presence of styrenes or indene results in formal [3 + 2] ad dition of the indole stabilised cation to the alkene to give cyclopent a[b]indoles with a high degree of stereoselectivity; use of methylcycl ohexene as the alkene component gave the cis-fused cyclopenta[b]indole 17, which was independently synthesised as its (-)-enantiomer from th e diketone 18.