Issue 19, 2022

P(v) intermediate-mediated E1cB elimination for the synthesis of glycals

Abstract

Glycals are highly versatile and useful building blocks in the chemistry of carbohydrate and natural products. However, the practical synthesis of glycals remains a long-standing and mostly unsolved problem in synthetic chemistry. Herein, we present an unprecedented approach to make a variety of glycals using phosphonium hydrolysis-induced, P(V) intermediate-mediated E1cB elimination. The method provides a highly efficient, practical and scalable strategy for the synthesis of glycals with good generality and excellent yields. Furthermore, the strategy was successfully applied to late-stage modification of complex drug-like molecules. Additionally, the corresponding 1-deuterium-glycals were produced easily by simple tBuONa/D2O-hydrolysis–elimination. Mechanistic investigations indicated that the oxaphosphorane intermediate-mediated E1cB mechanism is responsible for the elimination reaction.

Graphical abstract: P(v) intermediate-mediated E1cB elimination for the synthesis of glycals

Supplementary files

Article information

Article type
Edge Article
Submitted
10 Mar 2022
Accepted
22 Apr 2022
First published
22 Apr 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 5588-5596

P(V) intermediate-mediated E1cB elimination for the synthesis of glycals

F. Liu, H. Huang, L. Sun, Z. Yan, X. Tan, J. Li, X. Luo, H. Ding and Q. Xiao, Chem. Sci., 2022, 13, 5588 DOI: 10.1039/D2SC01423H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements