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Ni-Catalyzed Regioselective Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling and Application to the Concise Synthesis of Lignan Natural Products

Shekhar KC, Prakash Basnet, Surendra Thapa, Bijay Shrestha and Ramesh Giri*

*Department of Chemistry & Chemical Biology, The University of New Mexico, Albuquerque, New Mexico 87131, United States, Email: rgiriunm.edu

S. KC, P. Basnet, S. Thapa, B. Shrestha, R. Giri, J. Org. Chem., 2018, 83, 2920-2936.

DOI: 10.1021/acs.joc.8b00184 (free Supporting Information)


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Abstract

(terpy)NiBr2 catalyzes a regioselectively difunctionalisation of unactivated olefins with tethered alkyl halides and arylzinc reagents to provide (arylmethyl)carbo- and heterocyclic scaffolds. The reaction shows an excellent functional group tolerance (such as ketones, esters, nitriles, halides, and base-sensitive racemizable stereocenters).

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Key Words

cyclopentanes, pyrrolidines, tetrahydrofurans


ID: J42-Y2018