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Ligand-controlled C(sp(3))-H arylation and olefination in synthesis of unnatural chiral alpha-amino acids

Academic Article
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Overview

related to degree

  • He, Jian, Ph.D. in Chemistry, Scripps Research 2011 - 2016

authors

  • He, Jian
  • Li, S.
  • Deng, Y.
  • Fu, H.
  • Laforteza, B. N.
  • Spangler, J. E.
  • Homs, A.
  • Yu, Jin-Quan

publication date

  • March 2014

journal

  • Science  Journal

abstract

  • The use of ligands to tune the reactivity and selectivity of transition metal catalysts for C(sp(3))-H bond functionalization is a central challenge in synthetic organic chemistry. Herein, we report a rare example of catalyst-controlled C(sp(3))-H arylation using pyridine and quinoline derivatives: The former promotes exclusive monoarylation, whereas the latter activates the catalyst further to achieve diarylation. Successive application of these ligands enables the sequential diarylation of a methyl group in an alanine derivative with two different aryl iodides, affording a wide range of β-Ar-β-Ar'-α-amino acids with excellent levels of diastereoselectivity (diastereomeric ratio > 20:1). Both configurations of the β-chiral center can be accessed by choosing the order in which the aryl groups are installed. The use of a quinoline derivative as a ligand also enables C(sp(3))-H olefination of a protected alanine.

subject areas

  • Alanine
  • Alkenes
  • Amino Acids
  • Carbon
  • Catalysis
  • Hydrogen Bonding
  • Ligands
  • Palladium
  • Pyridines
  • Quinolines
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC4179246

International Standard Serial Number (ISSN)

  • 1095-9203 (Electronic) 0036-8075 (Linking)

Digital Object Identifier (DOI)

  • 10.1126/science.1249198

PubMed ID

  • 24626923
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Additional Document Info

start page

  • 1216

end page

  • 1220

volume

  • 343

issue

  • 6176

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