Issue 28, 2022

Manganese(iii)-promoted highly stereoselective phosphorylation of acyclic tertiary enamides to synthesize E-selective β-phosphoryl enamides

Abstract

A concise manganese(III)-promoted stereoselective β-phosphorylation of acyclic tertiary enamides and diverse H-phosphine oxides was achieved. This reaction proceeds with absolute E-selectivity in contrast to Z-selectivity obtained in other previous works and affords various E-selective β-phosphorylated tertiary enamides in high efficiency. To the best of our knowledge, this is the first case of E-selective β-phosphorylation of tertiary enamides through C–H functionalization. In addition, the method features broad substrate scope, good functional group compatibility and efficient scale-up.

Graphical abstract: Manganese(iii)-promoted highly stereoselective phosphorylation of acyclic tertiary enamides to synthesize E-selective β-phosphoryl enamides

Supplementary files

Article information

Article type
Paper
Submitted
22 May 2022
Accepted
28 Jun 2022
First published
01 Jul 2022

Org. Biomol. Chem., 2022,20, 5566-5574

Manganese(III)-promoted highly stereoselective phosphorylation of acyclic tertiary enamides to synthesize E-selective β-phosphoryl enamides

X. Xu, W. Li, Q. Li, S. Chen, X. Zhang, B. Yang and W. Wang, Org. Biomol. Chem., 2022, 20, 5566 DOI: 10.1039/D2OB00980C

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