Cl^–···H–N Interaction Assisted Addition of Sulfonamides to Enol Ethers: Synthesis of 2-Deoxy and 2,6-Dideoxy Sulfonamido Glycosides

Abstract

The strained/frustrated electrostatic interactions between the ion pair of TTBPy⁺X^– increases the reactivity in both the ions, resulting in the activation of a third molecule like sulfonamides (aromatic/­aliphatic) via hydrogen bonding. This intriguing weak-interactions-based reactivity has been utilized to develop an organocatalytic synthesis of 2-deoxy-sulfonamido-glycosides from glycals. The sulfonamidoglycosylation of glycals using a catalytic amount of 2,4,6-tri-tert-butylpyridinium salts proceeded stereoselectively to provide N-glycosides in good to high yields. This process was demonstrated with l-rhamnal and d-galactal. Besides, IR spectroscopic studies explain that the hindered protonated pyridine cannot behave as a cationic Brønsted acid as is generally perceived.

Key words

N-glycosylation - catalysis - strained Brønsted pairs - stereoselectivity - 2,4,6-tri-tert-butylpyridine.

Publication History

Received: 28 May 2022

Accepted after revision: 05 July 2022

Accepted Manuscript online:
05 July 2022

Article published online:
04 August 2022

• References and Notes

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