Copper-Phosphido Catalysis: Enantioselective Addition of Phosphines to Cyclopropenes

24 March 2023, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We describe a copper-catalyst that promotes the addition of phosphines to cyclopropenes at ambient temperature. A range of cyclopropylphosphines bearing different steric and electronic properties can now be accessed in high yields and enantioselectivities. A combined experimental and theoretical mechanistic study supports insertion of a Cu(I)-phosphido intermediate into the strained olefin. Density functional theory calculations reveal migratory insertion as the stereodetermining step of the pathway, with final product formation occurring via a syn-protodemetalation. Enrichment of phosphorus stereocenters is demonstrated via a DyKAT process.

Keywords

Hydrophosphination
DFT
Copper Catalysis
DyKAT

Supplementary materials

Title
Description
Actions
Title
Copper-Phosphido Catalysis: Enantioselective Addition of Phosphines to Cyclopropenes
Description
Reaction Protocols, Computational Protocols
Actions

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