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Diastereo- and Enantioselective Formal [3 + 2] Cycloaddition of Cyclopropyl Ketones and Alkenes via Ti-Catalyzed Radical Redox Relay

Wei Hao, Johannes H. Harenberg, Xiangyu Wu, Samantha N. MacMillan and Song Lin*

*Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States, Email: songlincornell.edu

W. Hao, J. H. Harenberg, X. Wu, S. N. MacMillan, S. Lin, J. Am. Chem. Soc., 2018, 140, 3514-3517.

DOI: 10.1021/jacs.7b13710 (free Supporting Information)


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Abstract

A stereoselective formal [3 + 2] cycloaddition of cyclopropyl ketones and radical-acceptor alkenes to form polysubstituted cyclopentane derivatives is catalyzed by a chiral Ti(salen) complex via a radical redox-relay mechanism. The cycloaddition constructs two C-C bonds and two contiguous stereogenic centers with generally excellent diastereo- and enantioselectivity.


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Key Words

cyclopentanes, manganese


ID: J48-Y2018