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Palladium(II)-catalyzed enantioselective C(sp(3))-H activation using a chiral hydroxamic acid ligand

Academic Article
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Overview

related to degree

  • Zhu, Ru-Yi, Ph.D. in Chemistry, Scripps Research 2013 - 2018
  • Wasa, Masayuki, Ph.D. in Chemistry, Scripps Research 2007 - 2012

authors

  • Xiao, K. J.
  • Lin, David Wei
  • Miura, M.
  • Zhu, Ru-Yi
  • Gong, W.
  • Wasa, Masayuki
  • Yu, Jin-Quan

publication date

  • June 2014

journal

  • Journal of the American Chemical Society  Journal

abstract

  • An enantioselective method for Pd(II)-catalyzed cross-coupling of methylene ?-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 ?-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 ?-chiral quaternary stereocenters. This new class of chiral catalysts also show promises for enantioselective ?-C(sp(3))-H activation of acyclic amides.
  • 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.

subject areas

  • Amides
  • Boron Compounds
  • Catalysis
  • Cyclobutanes
  • Hydroxamic Acids
  • Ligands
  • Palladium
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC4063184

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja504196j

PubMed ID

  • 24815880
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Additional Document Info

start page

  • 8138

end page

  • 8142

volume

  • 136

issue

  • 22

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