Open AccessPalladium(II)-Catalyzed Enantioselective C(sp3)–H Activation Using a Chiral Hydroxamic Acid Ligand
Author(s) -
KaiJiong Xiao,
David W. Lin,
Motofumi Miura,
RuYi Zhu,
Wei Gong,
Masayuki Wasa,
JinQuan Yu
Publication year - 2014
Publication title -
journal of the american chemical society
Language(s) - Uncategorized
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja504196j
Subject(s) - enantioselective synthesis , chemistry , stereocenter , palladium , catalysis , ligand (biochemistry) , chiral ligand , stereochemistry , reagent , hydroxamic acid , medicinal chemistry , combinatorial chemistry , organic chemistry , biochemistry , receptor
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.