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Formation of α-chiral centers by asymmetric β-C(sp3)–H arylation, alkenylation, and alkynylation

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Science  03 Feb 2017:
Vol. 355, Issue 6324, pp. 499-503
DOI: 10.1126/science.aal5175

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Expressed preferences among methyl groups

Targeting just one of the two equivalent branch ends in Y-shaped molecules is a particular challenge for catalysis. Enzymes manage to do it by grasping the whole molecule, octopus-like, but often enzymes cannot tolerate minor structural variations. Wu et al. produced an amide-directed palladium catalyst that, armed with oxazoline-derived chiral ligands, could reliably attack just one methyl member of isopropyl groups. The reaction successfully replaced C–H bonds with C–C bonds in a wide variety of aryl and vinyl coupling partners.

Science, this issue p. 499