Stereodivergent synthesis via iridium-catalyzed asymmetric double allylic alkylation of cyanoacetate.

ABSTRACT: Methods that enable the rapid construction of multiple C-C bonds using a single catalyst with high diastereo- and enantio-control are particularly valuable in organic synthesis. Here, we report an Ir-catalyzed double allylic alkylation reaction in which bisnucleophilic cyanoacetate reacted successionally with electrophilic π-allyl-Ir species, producing various pseudo-C ₂-symmetrical cyanoacetate derivatives in high yield with excellent stereocontrol. More challenging sequential allylic alkylation/allylic alkylation with two distinct allylic carbonates that can deliver the corresponding products bearing three contiguous tertiary-quaternary-tertiary stereocenters was also developed by using a modified catalytic system, which is revealed to be associated with the quasi

SUBMITTER: Shen C 

PROVIDER: S-EPMC8672708 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature