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Enantioselective Synthesis of Acyclic α‐Quaternary Carboxylic Acid Derivatives through Iridium‐Catalyzed Allylic Alkylation
Author(s) -
Shockley Samantha E.,
Hethcox J. Caleb,
Stoltz Brian M.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201707015
Subject(s) - stereocenter , enantioselective synthesis , tsuji–trost reaction , alkylation , chemistry , iridium , allylic rearrangement , catalysis , reagent , carboxylic acid , organic chemistry , cyanide , combinatorial chemistry
The first highly enantioselective iridium‐catalyzed allylic alkylation that provides access to products bearing an allylic all‐carbon quaternary stereogenic center has been developed. The reaction utilizes a masked acyl cyanide (MAC) reagent, which enables the one‐pot preparation of α‐quaternary carboxylic acids, esters, and amides with a high degree of enantioselectivity. The utility of these products is further explored through a series of diverse product transformations.