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Gold(I)-Catalyzed Cycloisomerization of 3-Alkoxyl-1,6-diynes: A?Facile Access to Bicyclo[2.2.1]hept-5-en-2-ones.

ABSTRACT: A novel gold-catalyzed cycloisomerization of 1,6-diynes was achieved, providing an atom-economic approach to a diverse set of bicyclo[2.2.1]hept-5-en-2-ones in moderate to good yields. With unsymmetrical starting materials with two different internal alkynyl substituents, to some extent, the regioselectivity could be controlled by both electronic and steric factors. This unprecedented reactivity pattern may inspire new and unconventional strategies for the preparation of bridged ring systems.

SUBMITTER: Hu C 

PROVIDER: S-EPMC7318145 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Gold(I)-Catalyzed Cycloisomerization of 3-Alkoxyl-1,6-diynes: A Facile Access to Bicyclo[2.2.1]hept-5-en-2-ones.

Hu Chao C   Wang Tao T   Rudolph Matthias M   Oeser Thomas T   Asiri Abdullah M AM   Hashmi A Stephen K ASK  

Angewandte Chemie (International ed. in English) 20200324 22

A novel gold-catalyzed cycloisomerization of 1,6-diynes was achieved, providing an atom-economic approach to a diverse set of bicyclo[2.2.1]hept-5-en-2-ones in moderate to good yields. With unsymmetrical starting materials with two different internal alkynyl substituents, to some extent, the regioselectivity could be controlled by both electronic and steric factors. This unprecedented reactivity pattern may inspire new and unconventional strategies for the preparation of bridged ring systems. ...[more]

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