Enantioselective α-Allylation of Acyclic Esters Using B(pin)-Substituted Electrophiles: Independent Regulation of Stereocontrol Elements through Cooperative Pd/Lewis Base Catalysis.

ABSTRACT: Cooperation between a Lewis base and Pd catalyst enables the direct enantioselective α-functionalization of aryl and vinyl acetic acid esters using a bifunctional B(pin)-substituted electrophile. Critical to the success of this method was the recognition that both catalysts could control the necessary stereochemical aspects; the Lewis base catalyst controls the enantioselectivity of the reaction, whereas the Pd catalyst regulates alkenyl-B(pin) configuration. This is the first example of using cooperative catalysis to control both stereochemical features during Pd-catalyzed allylic alkylation.

SUBMITTER: Scaggs WR 

PROVIDER: S-EPMC6515920 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature