Insights into the Gold‐Catalyzed Cycloisomerization of 3‐Allyl‐1, 4‐diynes for the Synthesis of Bicyclic Hydrocarbons. Issue 9 (1st March 2022)

• Record Type: Journal Article
• Authors: Yu, Jhen‐Kuei; Czekelius, Constantin
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 9(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-03-01
• Subjects: Catalysis -- Cyclopropanations -- Enynes -- Gold -- Rearrangements; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200027
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: An efficient protocol for the synthesis of 3‐ethynyl‐2‐aryl‐bicyclo[3.1.0]hexenes through a gold‐catalyzed enyne cyclization was established in this work. Depending on the specific substitution pattern, unusual cationic rearrangements of the corresponding gold carbene were revealed, leading to either cyclohexadienes or 5, 9‐methanobenzo[8]annulene derivatives, respectively. Abstract : Unexpected rearrangements are observed in the gold‐catalyzed isomerization of 3‐allyl‐1, 4‐diynes. Depending on the fourth substituent either bicyclo[3.1.0]hexanes, cyclohexadienes, or 5, 9‐methanobenzo[8]annulenes are obtained from the presumably first‐formed cyclohexenylidene gold intermediate.