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Zhao Y, Jin J, Boyle JW, et al. Silver-Catalyzed 1,3-Acyloxy Migration/Diels-Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines. J Org Chem. 2017;82(6):2826-2834doi: 10.1021/acs.joc.7b00048.
Zhao, Y., Jin, J., Boyle, J. W., Lee, B. R., Day, D. P., Susanti, D., Clarkson, G. J., & Chan, P. W. (2017). Silver-Catalyzed 1,3-Acyloxy Migration/Diels-Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines. The Journal of organic chemistry, 82(6), 2826-2834. https://doi.org/10.1021/acs.joc.7b00048
Zhao, Yichao, et al. "Silver-Catalyzed 1,3-Acyloxy Migration/Diels-Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines." The Journal of organic chemistry vol. 82,6 (2017): 2826-2834. doi: https://doi.org/10.1021/acs.joc.7b00048
Zhao Y, Jin J, Boyle JW, Lee BR, Day DP, Susanti D, Clarkson GJ, Chan PW. Silver-Catalyzed 1,3-Acyloxy Migration/Diels-Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines. J Org Chem. 2017 Mar 17;82(6):2826-2834. doi: 10.1021/acs.joc.7b00048. Epub 2017 Mar 07. PMID: 28225621.
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J Org Chem. 2017 Mar 17;82(6):2826-2834. doi: 10.1021/acs.joc.7b00048. Epub 2017 Mar 07.

Silver-Catalyzed 1,3-Acyloxy Migration/Diels-Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines.

The Journal of organic chemistry

Yichao Zhao, Jianwen Jin, Joshua William Boyle, Bo Ra Lee, David Philip Day, Dewi Susanti, Guy James Clarkson, Philip Wai Hong Chan

Affiliations

  1. School of Chemistry, Monash University , Clayton, Victoria 3800, Australia.
  2. Department of Chemistry, University of Warwick , Coventry CV4 7AL, United Kingdom.
  3. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , Singapore 637371, Singapore.

PMID: 28225621 DOI: 10.1021/acs.joc.7b00048

Abstract

A synthetic method to prepare partially hydrogenated isoquinolines efficiently from silver-mediated [3,3]-sigmatropic rearrangement/Diels-Alder reaction of 1,9-dien-4-yne esters is described. The reactions were shown to be robust with a wide variety of substitution patterns tolerated to provide the corresponding nitrogen-containing heterocyclic products in good to excellent yields. This includes examples containing a bridgehead sp

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