Stereoselective Access to Polyfunctionalized Nine‐Membered Heterocycles by Sequential Gold and Palladium Catalysis

We report herein a gold and palladium sequential catalysis system to access furan‐fused nine‐membered heterocycles in high efficiency and enantioselectivity. In this one‐pot procedure, easily accessible enynamides undergo cyclization to generate azadienes in situ that participate in enantioselective...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2021-06, Vol.60 (23), p.12775-12780
Main Authors: Yang, Guoqiang, Ke, Ya‐Ming, Zhao, Yu
Format: Article
Language:English
Subjects:
[5+4] cycloaddition
Carbonates
Catalysis
Conformation
Cycloaddition
Enantiomers
enantioselectivity
Gold
gold catalysis
medium-sized heterocycle
Palladium
palladium catalysis
Stereoselectivity
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Summary:We report herein a gold and palladium sequential catalysis system to access furan‐fused nine‐membered heterocycles in high efficiency and enantioselectivity. In this one‐pot procedure, easily accessible enynamides undergo cyclization to generate azadienes in situ that participate in enantioselective formal [5+4] cycloaddition with vinyl ethylene carbonates. Conformation‐controlled highly diastereoselective derivatizations of these medium‐sized rings, coupled with oxidative furan cleavage, have enabled the access to diverse densely‐functionalized nine‐membered lactams. We report herein a gold and palladium sequential catalysis to convert enynamides and vinyl ethylene carbonates to furan‐fused nine‐membered heterocycles via azadiene generation followed by [5+4] cycloaddition. Conformation‐controlled diastereoselective derivatizations of these medium‐sized rings and oxidative furan cleavage enabled access to diverse polyfunctionalized nine‐membered lactams.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202102061