Palladium(II)-Catalyzed Enantioselective Desymmetrizative Ring Opening of Oxabicyclic Alkenes with Alkynylanilines: Efficient Access to Enantioenriched Functionalized Cyclohexenes

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-03-20 DOI:10.1039/d5qo00118h

Binhong Tan, Junjie Meng, Qianru Liu, Shixin Chen, Mingyue Xue, Yue Zhang, Yuping Zhang, Zhaodong Li

引用次数: 0

Abstract

We disclose herein a pratical enantioselective desymmetrizative ring-opening coupling of oxabicyclic alkenes with alkynylanilines, enabled by Pd(II)-catalyzed aminopalladation cascade, to allow for the efficient access to a diverse set of indolated cyclohexenes bearing four contiguous densely functionalized carbon stereocenters in high yields with excellent diastereo- and enantioselectivities. Representative post-transformations to other valuable enantioenriched functionalized cyclohexene derivatives demonstrates the synthetic potential of this synthetic methodology.

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.