Copper Reactivity Can be Tuned to Catalyse the Stereoselective Synthesis of 2-Deoxy Glycosides from Glycals

04 October 2019, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We demonstrate that tuning the reactivity of Cu by the choice of oxidation state and counterion leads to the activation of both “armed” and “disarmed” type glycals towards direct glycosylation leading to the a-stereoselective synthesis of deoxyglycosides in good to excellent yields. Mechanistic studies show that CuI is essential for effective catalysis and stereocontrol and that the reaction proceeds through dual activation of both the enol ether as well as the OH nucleophile.

Keywords

Stereoselectivity
Glycosylation
Glycals
Enol ethers
Copper catalysis

Supplementary materials

Title
Description
Actions
Title
TOC
Description
Actions
Title
ESI COPPER GLYCOSYLATION260719( RJ comments 2 OCT(2)
Description
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.