4.8 Article

Asymmetric Synthesis of 1-Heteroaryl-1-arylalkyl Tertiary Alcohols and 1-Pyridyl-1-arylethanes by Lithiation-Borylation Methodology

Journal

ORGANIC LETTERS
Volume 15, Issue 6, Pages 1346-1349

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol400289v

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Funding

  1. EPSRC
  2. European Research Council (ERC) [246785]
  3. EPSRC [EP/E052185/1, EP/I038071/1, EP/K03927X/1] Funding Source: UKRI
  4. Engineering and Physical Sciences Research Council [EP/I038071/1, EP/K03927X/1, EP/E052185/1] Funding Source: researchfish

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The synthesis of highly enantioenriched alpha-heterocyclic tertiary alcohols has been achieved via lithiation-borylation of a configurationally stable lithiated carbamate and heterocyclic pinacol boronic esters followed by oxidation. Protodeboronation of the alpha-heterocyclic tertiary boronic esters using TBAF center dot 3H(2)O or CsF gave highly enantioenriched 1-pyridyl-1-arylethanes in high er.

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