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Luzung MR, Markham JP, Toste FD. Catalytic isomerization of 1,5-enynes to bicyclo[3.1.0]hexenes. J Am Chem Soc. 2004;126(35):10858-9doi: 10.1021/ja046248w.
Luzung, M. R., Markham, J. P., & Toste, F. D. (2004). Catalytic isomerization of 1,5-enynes to bicyclo[3.1.0]hexenes. Journal of the American Chemical Society, 126(35), 10858-9. https://doi.org/10.1021/ja046248w
Luzung, Michael R, et al. "Catalytic isomerization of 1,5-enynes to bicyclo[3.1.0]hexenes." Journal of the American Chemical Society vol. 126,35 (2004): 10858-9. doi: https://doi.org/10.1021/ja046248w
Luzung MR, Markham JP, Toste FD. Catalytic isomerization of 1,5-enynes to bicyclo[3.1.0]hexenes. J Am Chem Soc. 2004 Sep 08;126(35):10858-9. doi: 10.1021/ja046248w. PMID: 15339167.
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J Am Chem Soc. 2004 Sep 08;126(35):10858-9. doi: 10.1021/ja046248w.

Catalytic isomerization of 1,5-enynes to bicyclo[3.1.0]hexenes.

Journal of the American Chemical Society

Michael R Luzung, Jordan P Markham, F Dean Toste

Affiliations

  1. Center for New Directions in Organic Synthesis, Department of Chemistry, University of California-Berkeley, Berkeley, CA 94720, USA.

PMID: 15339167 DOI: 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.

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