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Palladium(II)-catalyzed enantioselective C(sp³)-H activation using a chiral hydroxamic acid ligand. | LitMetric

Palladium(II)-catalyzed enantioselective C(sp³)-H activation using a chiral hydroxamic acid ligand.

J Am Chem Soc

Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, United States.

Published: June 2014

AI Article Synopsis

Article Abstract

An enantioselective method for Pd(II)-catalyzed cross-coupling of methylene β-C(sp(3))-H bonds in cyclobutanecarboxylic acid derivatives with arylboron reagents is described. High yields and enantioselectivities were achieved through the development of chiral mono-N-protected α-amino-O-methylhydroxamic acid (MPAHA) ligands, which form a chiral complex with the Pd(II) center. This reaction provides an alternative approach to the enantioselective synthesis of cyclobutanecarboxylates containing α-chiral quaternary stereocenters. This new class of chiral catalysts also show promises for enantioselective β-C(sp(3))-H activation of acyclic amides.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4063184PMC
http://dx.doi.org/10.1021/ja504196jDOI Listing

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