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Enantioselective Conia-Ene-Type Cyclizations of Alkynyl Ketones through Cooperative Action of B(C6F5)3, N-Alkylamine and a Zn-Based Catalyst

Min Cao, Ahmet Yesilcimen, Masayuki Wasa*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email:

M. Cao, A. Yesilcimen, M. Wasa, J. Am. Chem. Soc., 2019, 141, 4199-4203.

DOI: 10.1021/jacs.8b13757

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A combination of B(C6F5)3, an N-alkylamine and a BOX-ZnI2 complex catalyzes an efficient and highly enantioselective Conia-ene-type process. Through cooperative action of B(C6F5)3 and amine, ketones can be converted in situ to the corresponding enolates. A subsequent enantioselective cyclization involving a BOX-ZnI2-activated alkyne provides various cyclopentenes in very good yield.

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Key Words

cyclopentenes, Conia-Ene reaction

ID: J48-Y2019