Catalaytic Isomerization of 1,5-Enynes to Bicyclo[3.1.0]hexenes
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- 13 August 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (35) , 10858-10859
- https://doi.org/10.1021/ja046248w
Abstract
The cycloisomerization of 1,5-enynes catalyzed by cationic triphenylphosphinegold(I) complexes produces bicyclo[3.1.0]hexenes. Substitution at all positions of the 1,5-enyne is tolerated, leading to a wide range of bicyclo[3.1.0]hexane structures, including those containing quaternary carbons. Substrates containing a 1,2-disubstituted olefin undergo stereospecific cycloisomerization (cis-olefin produces cis-cyclopropane, and trans-olefin gives trans-cyclopropane). Additionally, enantioenriched bicyclo[3.1.0]hexenes can be obtained from the gold(I)-catalyzed cycloisomerization of enantioenriched 1,5-enynes with excellent chirality transfer. The preparation of tricyclic systems is accomplished through a gold(I)-catalyzed tandem cycloisomerization−ring enlargement reaction.Keywords
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