NHC-Ni catalyzed 1,3- and 1,4-diastereodivergent heterocycle synthesis from hetero-substituted enyne.

Xuefeng Yong, Weiwei Gao, Xiulian Lin, Chun-Yu Ho

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Article in Communications chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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4 authors.

Xuefeng YongSchool of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin, (150001), Heilongjiang, China.ORCID http://orcid.org/0000-0002-6506-8845

Weiwei GaoSchool of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin, (150001), Heilongjiang, China.

Xiulian LinShenzhen Grubbs Institute, Guangdong Provincial Key Laboratory of Catalysis, Department of Chemistry, Southern University of Science and Technology (SUSTech), Shenzhen, (518055), Guangdong, China.

Chun-Yu HoShenzhen Grubbs Institute, Guangdong Provincial Key Laboratory of Catalysis, Department of Chemistry, Southern University of Science and Technology (SUSTech), Shenzhen, (518055), Guangdong, China. jasonhcy@sustech.edu.cn.ORCID http://orcid.org/0000-0002-1064-8682

Funding

National Natural Science Foundation of China (National Science Foundation of China) 21602099Shenzhen Science and Technology Innovation Commission C17783101Shenzhen Science and Technology Innovation Commission JCYJ 20170817105041557

6 · The paper itself

Abstract

Diastereodivergent heterocycle synthesis has been recognized as an important tool for drug discovery in recent years, yet strategies based on nickelacycle formation have not been established. Here, we report a NHC-Ni catalyzed highly 1,3- and 1,4-diastereodivergent heterocycle synthesis from enyne, which is achieved by manipulating the enyne N-substituent (allowing switching of selectivity from up to 2:98 to 98:2). The key to success is the efficient diastereodivergent formation of a nickelacyclopentene, with broad enyne scope at mild conditions, which subsequently provides reductive hydroalkenylation, acylation and silylation products on demand. Diastereoisomers which are sterically hard to distinguish or difficult to access by conventional routes are now accessible easily, including those with very similar 4°, contiguous and skipped stereocenters.

Identifiers

PMID36703443

DOI10.1038/s42004-020-0299-9

PMCPMC9814851

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