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. 2021 Jun 1;60(23):12775-12780.
doi: 10.1002/anie.202102061. Epub 2021 May 5.

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

Guoqiang Yang  1 , Ya-Ming Ke  1 , Yu Zhao  1   2
Affiliations

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

Guoqiang Yang et al. Angew Chem Int Ed Engl. .

Abstract

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.

Keywords: [5+4] cycloaddition; enantioselectivity; gold catalysis; medium-sized heterocycle; palladium catalysis.

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