Enantioselective cyanation via radical-mediated C-C single bond cleavage for synthesis of chiral dinitriles.

ABSTRACT: Ring-opening reaction via selective cleavage of C-C bond is known as a powerful strategy for construction of complex molecules. Complementary to the ionic process focusing on mostly small ring systems, radical-mediated C-C bond cleavage offers a solution for further diverse enantioselective functionalization benefited from its mild conditions, whereas such asymmetric transformations are still limited to three-membered rings so far. Herein, we describe radical-mediated ring-opening and enantioselective cyanation of four- and five-membered cycloketone oxime esters to access chiral 1,5- and 1,6-dinitriles. Employment of dual photoredox/copper catalysis is essential for the asymmetric ring-opening cyanation of cyclopentanone oxime esters. Both reactions proceed under mild conditions giving chi

SUBMITTER: Wang T 

PROVIDER: S-EPMC6879615 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature