Enantioselective Syntheses of (+)-Sertraline and (+)-Indatraline Using Lithiation/Borylation-Protodeboronation Methodology

Stefan Roesner, Javier Mansilla Casatejada, Tim G. Elford, Ravindra P. Sonawane, Varinder K. Aggarwal*

*Corresponding author for this work

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

71 Citations (Scopus)

Abstract

The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCI, H2O), or a solvent switch to CHCI3, to achieve high yields and high selectivities.

Original languageEnglish
Pages (from-to)5740-5743
Number of pages4
JournalOrganic Letters
Volume13
Issue number21
DOIs
Publication statusPublished - 4 Nov 2011

Keywords

  • TERTIARY BORONIC ESTERS
  • ASYMMETRIC-SYNTHESIS
  • ELECTROPHILIC SUBSTITUTION
  • SECONDARY ALCOHOLS
  • SERTRALINE
  • DIASTEREOSELECTIVITY
  • GENERATION
  • CONVERSION
  • REDUCTION
  • SEROTONIN

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