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Enantioselective Synthesis of Acyclic ?-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation.

ABSTRACT: 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 ?-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.

SUBMITTER: Shockley SE

PROVIDER: S-EPMC5674796 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation.

Shockley Samantha E SE Hethcox J Caleb JC Stoltz Brian M BM

Angewandte Chemie (International ed. in English) 20170809 38

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. ...[more]

PMID: 28722280

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