Scale-Up of a Rh-Catalyzed Asymmetric sp³-sp² Suzuki-Miyaura-Type Reaction.

ABSTRACT: Csp²-Csp² Suzuki-Miyaura couplings (SMCs) are ubiquitous in the synthesis of small molecules, but analogous Csp²-Csp³ bond-forming SMCs are rare, especially asymmetric variants. Recently, we developed a series of Rh-catalyzed couplings between racemic sp³-hybridized allyl chlorides and heteroaryl boronic acids. Here, we demonstrate that these catalytic asymmetric reactions can be scaled-up to give over 100 g of a product. The reaction we chose to test couples a heteroaromatic boronic acid derivative and a racemic bicyclic electrophile to give a product with three contiguous stereogenic centers. The SMC product was obtained as a single diastereomer in 90% yield and 98% ee. Kinetic analysis of the reaction reveals two exothermic steps in

SUBMITTER: Cunningham L 

PROVIDER: S-EPMC9680029 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature