Construction of Si-Stereogenic Silanols via Enantioselective Pd-Catalyzed C–H Alkenylation

17 August 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The construction of silicon-stereogenic silanols via the Pd-catalyzed intermolecular C–H alkenylation with the assistance of a commercially available L-pyroglutamic acid has been realized for the first time. Employing the oxime ether as the directing group, the silicon-stereogenic silanol derivatives could be readily prepared with excellent enantioselectivities, featuring a broad substrate scope and good functional group tolerance. Mechanistic studies indicate that L-pyroglutamic acid could stabilize the Pd catalyst and provide excellent chiral induction. Preliminary computational studies unveil the origin of the enantioselectivity in the C–H bond activation step.

Keywords

silicon-stereogenic
silanol
palladium
C–H alkenylation
MPAA ligand

Supplementary materials

Title
Description
Actions
Title
Supporting Information-PdCHAlkenylationSilanol
Description
supporting information including data and spectra
Actions

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