Catalytic isomerization of 1,5-enynes to bicyclo[3.1.0]hexenes |
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Authors: | Luzung Michael R Markham Jordan P Toste F Dean |
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Institution: | Center for New Directions in Organic Synthesis, Department of Chemistry, University of California-Berkeley, Berkeley, CA 94720, USA. |
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Abstract: | The cycloisomerization of 1,5-enynes catalyzed by cationic triphenylphosphinegold(I) complexes produces bicyclo3.1.0]hexenes. Substitution at all positions of the 1,5-enyne is tolerated, leading to a wide range of bicyclo3.1.0]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 bicyclo3.1.0]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. |
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