Asymmetric Synthesis of Tertiary Alcohols and Thiols via Nonstabilized Tertiary α‐Oxy‐ and α‐Thio‐Substituted Organolithium Species. (7th August 2017)

• Record Type: Journal Article
• Authors: Pulis, Alexander P.; Varela, Ana; Citti, Cinzia; Songara, Pradip; Leonori, Daniele; Aggarwal, Varinder K.
• Is Part Of: Angewandte Chemie. Volume 129:Number 36(2017)
• Page Start: 10975
• Page End: 10979
• Publication Date: 2017-08-07
• Subjects: Chirale Organolithiumspezies -- IR-Spektroskopie -- Tertiäre Alkohole -- Tertiäre Thiole; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201706722
• Languages: English
• ISSNs: 0044-8249

Abstract

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.