Asymmetric Synthesis of Tertiary Alcohols and Thiols via Nonstabilized Tertiary α-Oxy- and α-Thio-Substituted Organolithium Species

Research output: Contribution to journalArticle

  • External authors:
  • Ana Varela
  • Cinzia Citti
  • Pradip Songara
  • Daniele Leonori
  • Varinder K Aggarwal

Abstract

Nonstabilized α-O-substituted tertiary organolithium species are difficult to generate, and the α-S-substituted analogues are configurationally unstable. We now report that they can both be generated easily and trapped with a range of electrophiles with high enantioselectivity, providing ready access to a range of enantioenriched tertiary alcohols and thiols. The configurational stability of the α-S-organolithium species was enhanced by using a less coordinating solvent and short reaction times.

Bibliographical metadata

Original languageEnglish
Pages (from-to)10835-10839
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number36
Early online date7 Aug 2017
DOIs
Publication statusPublished - 23 Aug 2017

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