Catalytic Stereoconvergent Synthesis of Homochiral β-CF₃, β-SCF₃, and β-OCF₃ Benzylic Alcohols.

ABSTRACT: We describe an efficient catalytic strategy for enantio- and diastereoselective synthesis of homochiral β-CF₃, β-SCF₃, and β-OCF₃ benzylic alcohols. The approach is based on dynamic kinetic resolution (DKR) with Noyori-Ikariya asymmetric transfer hydrogenation leading to simultaneous construction of two contiguous stereogenic centers with up to 99.9% ee, up to 99.9:0.1 dr, and up to 99% isolated yield. The origin of the stereoselectivity and racemization mechanism of DKR is rationalized by density functional theory calculations. Applicability of the previously inaccessible chiral fluorinated alcohols obtained by this method in two directions is further demonstrated: As building blocks for pharmaceuticals, illustrated by the synthesis of heat shock protein 9

SUBMITTER: Cotman AE 

PROVIDER: S-EPMC9542724 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature