PerspectiveOrganic Chemistry

Stitching two chiral centers with one catalyst

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Science  31 Jan 2020:
Vol. 367, Issue 6477, pp. 509-510
DOI: 10.1126/science.aba4222

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Transition metal–based catalysts can chaperone carbon-carbon (C–C) bond formation between an electrophilic and a (usually) nucleophilic partner. Reactions such as the palladium (Pd)–based Suzuki–Miyaura cross-coupling rival amide-bond formation in frequency of use (1). Such Pd-based cross-couplings join unsaturated carbon atoms, as in aryl-aryl couplings, but many recent efforts have focused on alkyl-alkyl cross-couplings (2). Chiral nickel (Ni)–based catalysts have enabled both efficient C–C bond formation as well as control over the stereochemistry of a stereocenter on the electrophilic-partner alkyl group. Similar control has only been demonstrated for a single cyclic nucleophilic partner, and this nucleophile has also been needed for the selective formation of stereocenters on both alkyl fragments. On page 559 of this issue, Huo et al. (3) demonstrate that a single chiral Ni catalyst can join two alkyl groups with high levels of control over the orientations of the neighboring stereocenters.

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