Enantioselective and Regiodivergent Gold and Chiral Brønsted Acid Catalyzed Cycloisomerization/Diels-Alder Reaction of 1,10-Dien-4-yn-3-yl Acetates: Synthesis of Norbornene-Embedded Tricarbocycles

Andrés Felipe León Rojas; Ying Yan Chong; Sara Helen Kyne; Bo Xia; Philip Wai Hong Chan

doi:10.1021/acs.orglett.4c00621

Enantioselective and Regiodivergent Gold and Chiral Brønsted Acid Catalyzed Cycloisomerization/Diels-Alder Reaction of 1,10-Dien-4-yn-3-yl Acetates: Synthesis of Norbornene-Embedded Tricarbocycles

Org Lett. 2024 Apr 19;26(15):3037-3042. doi: 10.1021/acs.orglett.4c00621. Epub 2024 Apr 1.

Authors

Andrés Felipe León Rojas¹, Ying Yan Chong¹, Sara Helen Kyne², Bo Xia^{3

1}, Philip Wai Hong Chan^{3

1}

Affiliations

¹ School of Chemistry, Monash University, Clayton, Victoria 3800, Australia.
² School of Chemistry, University of New South Wales, Sydney, New South Wales 2052, Australia.
³ Department of the Biological Environment, Jiyang College of Zhejiang A&F University, Zhuji 311800, China.

PMID: 38557076
DOI: 10.1021/acs.orglett.4c00621

Abstract

A synthetic method for the enantioselective and regiodivergent synthesis of hexahydro-2H-2,4a-methanonaphthalen-4-yl and octahydro-2,4-methanoazulen-1-yl esters that relies on the gold(I)- and chiral Brønsted acid-catalyzed cycloisomerization/Diels-Alder (CDA) reaction of (E)-1,10-dien-4-yn-3-yl acetates is described.