Inverting External Asymmetric Induction via Selective Energy Transfer Catalysis: A Strategy to β-Chiral Phosphonate Antipodes.

ABSTRACT: Enantiodivergent, catalytic reduction of activated alkenes relays stereochemical information encoded in the antipodal chiral catalysts to the pro-chiral substrate. Although powerful, the strategy remains vulnerable to costs and availability of sourcing both catalyst enantiomers. Herein, a stereodivergent hydrogenation of α,β-unsaturated phosphonates is disclosed using a single enantiomer of the catalyst. This enables generation of the R- or S-configured β-chiral phosphonate with equal and opposite selectivity. Enantiodivergence is regulated at the substrate level through the development of a facile E → Z isomerisation. This has been enabled for the first time by selective energy transfer catalysis using anthracene as an inexpensive organic photosensitiser. Synthetically valuable in its own

SUBMITTER: Onneken C 

PROVIDER: S-EPMC6972697 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature