Stereocontrolled Substitution at P(III) Centers Enabled by Pyridine N-Oxide Catalysis.

Authors

Bingbing Dong, Zhongxian Li, Yuanyuan Yin, Shiqing Huang, Yonggui Robin Chi

Published in

Organic letters. Jun 23, 2026. Epub Jun 23, 2026.

Abstract

A P(III)-based stereoselective substitution of phosphorodiamidites catalyzed by chiral pyridine N-oxide catalysts is disclosed. Unlike acid-promoted systems that suffer from stereorandom products and phosphites via uncontrolled multiple substitutions, this approach enables selective monosubstitution to deliver configurationally defined phosphoramidites (up to 4:96 dr). This enables stereoselective phosphitylation of various bioactive molecules, such as simvastatin, estradiol, uridine, and adenosine. Mechanistic studies supported by DFT calculations reveal a water-assisted covalent catalytic pathway.

PMID:
42335372
Bibliographic data and abstract were imported from PubMed on 24 Jun 2026.

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