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Asymmetric Synthesis of Tertiary Alcohols and Thiols via Nonstabilized Tertiary α‐Oxy‐ and α‐Thio‐Substituted Organolithium Species
Author(s) -
Pulis Alexander P.,
Varela Ana,
Citti Cinzia,
Songara Pradip,
Leonori Daniele,
Aggarwal Varinder K.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201706722
Subject(s) - tertiary alcohols , chemistry , thio , electrophile , organolithium compounds , tertiary amine , tertiary care , organic chemistry , solvent , combinatorial chemistry , alcohol , catalysis , medicine , ion , family medicine , deprotonation
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.