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Kulandai Raj AS, Kale BS, Mokar BD, et al. Gold-Catalyzed N,O-Functionalizations of 6-Allenyl-1-ynes with N-Hydroxyanilines To Construct Benzo[b]-azepin-4-one Cores. Org Lett. 2017;19(19):5340-5343doi: 10.1021/acs.orglett.7b02629.
Kulandai Raj, A. S., Kale, B. S., Mokar, B. D., & Liu, R. S. (2017). Gold-Catalyzed N,O-Functionalizations of 6-Allenyl-1-ynes with N-Hydroxyanilines To Construct Benzo[b]-azepin-4-one Cores. Organic letters, 19(19), 5340-5343. https://doi.org/10.1021/acs.orglett.7b02629
Kulandai Raj, Antony Sekar, et al. "Gold-Catalyzed N,O-Functionalizations of 6-Allenyl-1-ynes with N-Hydroxyanilines To Construct Benzo[b]-azepin-4-one Cores." Organic letters vol. 19,19 (2017): 5340-5343. doi: https://doi.org/10.1021/acs.orglett.7b02629
Kulandai Raj AS, Kale BS, Mokar BD, Liu RS. Gold-Catalyzed N,O-Functionalizations of 6-Allenyl-1-ynes with N-Hydroxyanilines To Construct Benzo[b]-azepin-4-one Cores. Org Lett. 2017 Oct 06;19(19):5340-5343. doi: 10.1021/acs.orglett.7b02629. Epub 2017 Sep 26. PMID: 28949545.
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Org Lett. 2017 Oct 06;19(19):5340-5343. doi: 10.1021/acs.orglett.7b02629. Epub 2017 Sep 26.

Gold-Catalyzed N,O-Functionalizations of 6-Allenyl-1-ynes with N-Hydroxyanilines To Construct Benzo[b]-azepin-4-one Cores.

Organic letters

Antony Sekar Kulandai Raj, Balaji S Kale, Bhanudas Dattatray Mokar, Rai-Shung Liu

Affiliations

  1. Department of Chemistry, National Tsing-Hua University , Hsinchu, 30013, Taiwan, ROC.

PMID: 28949545 DOI: 10.1021/acs.orglett.7b02629

Abstract

Gold-catalyzed reactions of 6-allen-1-ynes with N-hydroxyanilines afford thermally stable benzoazepin-4-ones in anti-selectivity; these anti-configured products are easily isomerized to their syn-isomers on a silica column. The mechanism of reactions likely involve initial nitrone/allene cycloadditions, followed by skeletal rearrangement of resulting intermediates.

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