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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
Author(s) -
Hu Chao,
Wang Tao,
Rudolph Matthias,
Oeser Thomas,
Asiri Abdullah M.,
Hashmi A. Stephen K.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201914284
Subject(s) - cycloisomerization , steric effects , bicyclic molecule , regioselectivity , chemistry , reactivity (psychology) , catalysis , ring (chemistry) , electronic effect , stereochemistry , alkoxy group , combinatorial chemistry , medicinal chemistry , organic chemistry , medicine , alternative medicine , pathology , alkyl
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.