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

Charlotte G. Watson, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

29 Citations (Scopus)
408 Downloads (Pure)

Abstract

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.

Original languageEnglish
Pages (from-to)1346-1349
Number of pages4
JournalOrganic Letters
Volume15
Issue number6
Early online date5 Mar 2013
DOIs
Publication statusPublished - 15 Mar 2013

Keywords

  • CHIRAL SECONDARY ALCOHOLS
  • ENANTIOSELECTIVE ADDITION
  • ELECTROPHILIC SUBSTITUTION
  • TITANIUM(IV) CATALYST
  • STEREOGENIC CENTERS
  • GRIGNARD-REAGENTS
  • BORONIC ESTERS
  • KETONES
  • DERIVATIVES
  • DIALKYLZINC

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