Gold self-relay catalysis for accessing functionalized cyclopentenones bearing an all-carbon quaternary stereocenter

A new gold(i) self-relay catalysis consisting of a 3,3-rearrangement, Nazarov cyclization and Michael addition cascade of 1,3-enyne acetates with aurones and their derived azadienes is reported, and used to produce a series of densely functionalized cyclopentenones bearing a cyclic quaternary stereo...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 9; no. 1; pp. 140 - 146
Main Authors Meng, Fan-Tao, Chen, Jing-Long, Qin, Xiao-Yan, Zhang, Tian-Shu, Tu, Shu-Jiang, Jiang, Bo, Hao, Wen-Juan
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.12.2021
Royal Society of Chemistry
Subjects
Acetates
Acetic acid
Carbon
Catalysis
Catalytic converters
Chemistry
Chemistry, Organic
Functional groups
Gold
Inert atmospheres
Organic chemistry
Physical Sciences
Regioselectivity
Relay
Science & Technology
Substrates
REARRANGEMENT
PROPARGYLIC ESTERS
CARBENES
SIGMA
SEQUENCE
EFFICIENT SYNTHESIS
CYCLOISOMERIZATION
PI
CYCLIZATION
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Summary:A new gold(i) self-relay catalysis consisting of a 3,3-rearrangement, Nazarov cyclization and Michael addition cascade of 1,3-enyne acetates with aurones and their derived azadienes is reported, and used to produce a series of densely functionalized cyclopentenones bearing a cyclic quaternary stereocenter in moderate to good yields under mild conditions. This tandem protocol demonstrates high regioselectivity, broad substrate flexibility and good functional group tolerance of substrates without inert atmosphere protection, providing a catalytic and convergent approach for creating all-carbon stereoscopic centers.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d1qo01313k