Palladium(II)-Catalyzed Enantioselective C(sp3)–H Activation Using a Chiral Hydroxamic Acid Ligand | Zendy

KaiJiong Xiao | Zendy; David W. Lin | Zendy; Motofumi Miura | Zendy; RuYi Zhu | Zendy; Wei Gong | Zendy; Masayuki Wasa | Zendy; JinQuan Yu | Zendy

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Palladium(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.

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