Enantioselective Functionalization of Primary C–H Bonds
Design of Catalysts for Site-Selective and Enantioselective Functionalization of Non-activated Primary C–H Bonds.
Nat. Chem. 2018;
18 October 2018 (online)
The authors previously described Rh-catalyzed functionalizations of secondary or tertiary C–H bonds (Liao et al. Nature 2016, 533, 230; Liao et al. Nature 2017, 551, 609). By tuning the catalyst, non-activated primary C–H bonds are functionalized with excellent site and enantioselectivities.
Subjecting chiral substrates to the reaction conditions allows access to either set of diastereomeric products when the appropriate catalyst enantiomer is employed. Stigmasteryl acetate could be selectively functionalized at its most sterically accessible primary C–H bond.