Transient-axial-chirality controlled asymmetric rhodium-carbene C(sp²)-H functionalization for the synthesis of chiral fluorenes.

ABSTRACT: In catalytic asymmetric reactions, the formation of chiral molecules generally relies on a direct chirality transfer (point or axial chirality) from a chiral catalyst to products in the stereo-determining step. Herein, we disclose a transient-axial-chirality transfer strategy to achieve asymmetric reaction. This method relies on transferring point chirality from the catalyst to a dirhodium carbene intermediate with axial chirality, namely a transient-axial-chirality since this species is an intermediate of the reaction. The transient chirality is then transferred to the final product by C(sp²)-H functionalization reaction with exceptionally high enantioselectivity. We also generalize this strategy for the asymmetric cascade reaction involving dual carbene/alkyne metathesis (CAM)

SUBMITTER: Dong K 

PROVIDER: S-EPMC7217916 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature