Chiral Diaryliodonium Phosphate Enables Light Driven Diastereoselective α-C(sp³)-H Acetalization.

ABSTRACT: C(sp³)-H bond functionalization has emerged as a robust tool enabling rapid construction of molecular complexity from simple building blocks, and the development of asymmetric versions of this reaction creates a powerful methodology to access enantiopure sp³-rich materials. Herein, we report the stereoselective functionalization of C(sp³)-H bonds of cyclic ethers employing a photochemically active diaryliodonium salt in combination with an anionic phase-transfer catalyst. The synthetic strategy outlined herein allows for regio- and stereochemical control in the α-C-H acetalization of furans and pyrans using alcohol nucleophiles, thus providing the ability to control the configuration at the stereogenic exocyclic acetal carbon.

SUBMITTER: Ye B 

PROVIDER: S-EPMC6448391 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature