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

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 ac...

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Bibliographic Details
Published inOrganic letters Vol. 26; no. 15; pp. 3037 - 3042
Main Authors León Rojas, Andrés Felipe, Chong, Ying Yan, Kyne, Sara Helen, Xia, Bo, Chan, Philip Wai Hong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.04.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BRONSTED ACID
DIENES
RAUTENSTRAUCH REARRANGEMENT
ALLENES
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00621