Highly Diastereoselective [3+2] Cyclopenta[ b ]annulation of Indoles with2‐Arylcyclopropyl Ketones and Diesters | Zendy

Venkatesh Chelvam | Zendy; Singh Prabal P. | Zendy; Ila Hiriyakkanavar | Zendy; Junjappa Hiriyakkanavar | Zendy

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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)

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