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Formal [3+2] Addition of Acceptor‐Substituted Cyclopropylmethylsilanes with Aryl Acetylenes
Author(s) -
Yadav Veejendra K.,
Sriramurthy Vardhineedi
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200453823
Subject(s) - synthon , cyclopentene , aryl , chemistry , acceptor , formal synthesis , medicinal chemistry , stereochemistry , organic chemistry , catalysis , alkyl , physics , condensed matter physics
Push–pull substitution of cyclopropanes can make these compounds synthetic equivalents of 1,3‐dipolar synthons 2 , suitable for formal [3+2] addition reactions with aryl acetylenes. Upon treatment with TiCl 4 , tert ‐butyldiphenylsilylmethyl‐substituted cyclopropyl ketones 1 reacted with aryl acetylenes to furnish cyclopentene derivatives 3 regio‐ and stereoselectively. R= n Bu, t Bu, Ph.