SYNTHESIS OF CYCLOPENT[B]INDOLES BY FORMAL [3-ADDITION OF INDOLYLMETHYL CATIONS TO ALKENES(2])

Authors
HARRISON CA LEINEWEBER R MOODY CJ WILLIAMS JMJ
Citation
Ca. Harrison et al., SYNTHESIS OF CYCLOPENT[B]INDOLES BY FORMAL [3-ADDITION OF INDOLYLMETHYL CATIONS TO ALKENES(2]), Tetrahedron letters, 34(52), 1993, pp. 8527-8530
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
52
Year of publication
1993
Pages
8527 - 8530
Database
ISI
SICI code
0040-4039(1993)34:52<8527:SOCBF[>2.0.ZU;2-G
Abstract
Treatment of indole-2- or 3-methanols with tin(IV) chloride as Lewis a cid in the presence of styrenes results informal [3+2]-addition of the indole stabilised cation to the alkene io give cyclopent[b]indoles wi th a high degree of stereoselectivity; use of methylcyclohexene as the alkene component gave the cis-fused cyclopent[b]indole 17, which was independently synthesised in enantiomerically pure form from the diket one 18.