Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines
Chung-Yang (Dennis) Huang and Abigail G. Doyle*
*Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States, Email: agdoyleprinceton.edu
C.-Y. Huang, A. G. Doyle, J. Am. Chem. Soc., 2012, 134, 9541-9544.
DOI: 10.1021/ja3013825 (free Supporting Information)
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A cross-coupling reaction between N-sulfonyl aziridines and organozinc reagents is possible under mild and functional-group-tolerant conditions in the presence of inexpensive and air-stable Ni(II) source and dimethyl fumarate as ligand to yield β-substituted amines. The stereoselectivity of the reaction is consistent with a stereoconvergent mechanism wherein the sulfonamide directs C-C bond formation.
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C.-Y. Huang, A. G. Doyle, J. Am. Chem. Soc., 2015, 137, 5638-5641.