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Highly Diastereoselective [3+2] Cyclopenta[ b ]annulation of Indoles with2‐Arylcyclopropyl Ketones and Diesters
Author(s) -
Venkatesh Chelvam,
Singh Prabal P.,
Ila Hiriyakkanavar,
Junjappa Hiriyakkanavar
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600342
Subject(s) - chemistry , propellane , annulation , cycloaddition , lewis acids and bases , stereochemistry , bicyclic molecule , medicinal chemistry , organic chemistry , catalysis
A highly diastereoselective Lewis acid (BF 3 · Et 2 O or TiCl 4 ) induced [3+2] cycloaddition of substituted and unsubstituted indoles with 2‐arylcyclopropyl ketones/diesters yielding cyclopenta[ b ]indoles in high yields is reported. This methodology has also been extended to tetrahydrocarbazole, cyclopenta[ b ]‐ and cyclohepta[ b ]indoles affording tetracyclic propellane type frameworks in modest yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)