Premium
Bismuth(III) Chloride Catalyzed Cycloisomerization of Enynes
Author(s) -
Wang Zezhou,
Fang Shiyue
Publication year - 2009
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.200900819
Subject(s) - cycloisomerization , chemistry , bismuth , isomerization , catalysis , lewis acids and bases , pyrrolidine , organic chemistry , chloride , reaction conditions , combinatorial chemistry
Several simple bismuth(III) salts were screened for the suitability to catalyze the cycloisomerization of enynes. Among them, BiCl 3 gave the best results. Under the optimized reaction conditions, eight substrates were studied, and acceptable to excellent isolated yields were obtained. Consistent with data in the literature, electron‐deficient alkynes were found to be better substrates for the reaction than electron‐rich ones. Because BiCl 3 is readily available, inexpensive and environmentally benign, this soft Lewis acid catalyzed isomerization reaction is expected to be a good choice for organic chemists to prepare pyrrolidine derivatives.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)