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

Alex Pulis, Ana Varela, Cinzia Citti, Pradip Songara, Daniele Leonori, Varinder Aggarwal

Research output: Contribution to journalArticle (Academic Journal)

5 Citations (Scopus)
272 Downloads (Pure)

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.
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 - 28 Aug 2017

Structured keywords

  • BCS and TECS CDTs

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