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Publications

Journal Article Ppublish 3 citations

PubMed: 41807174 DOI: 10.1016/j.scib.2026.02.049

Stereogenic P(V) platform construction via streamlined installation.

Sci Bull (Beijing) 71(8):1957-1967

Authors: Jing-Ming Zhang, Shi-Feng Tao, Xing-Kai Zhao, Han Yang, Gong Xu, Zhi-Tao He

Affiliations

  • School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, China; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.
  • Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Key Laboratory of Integrated Pest Management on the Loess Plateau of Ministry of Agriculture and Rural Affairs, College of Plant Protection, Northwest A&F University, Yangling 712100, China.
  • Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Key Laboratory of Integrated Pest Management on the Loess Plateau of Ministry of Agriculture and Rural Affairs, College of Plant Protection, Northwest A&F University, Yangling 712100, China.
  • School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, China; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.

Abstract

Molecules bearing a fully heteroatom-substituted phosphorus(V) stereocenter exist ubiquitously in medicines, agroscience and catalysis fields. Due to the lack of efficient and robust catalytic asymmetric methods, approaches to achieve fully heteroatom-substituted phosphorus(V) stereocenters usually rely on conventional chiral auxiliary control and resolution pathways. Recent catalytic protocols are built on tedious stepwise synthesis from complex P(V) precursors. Here, we report a streamlined installation strategy to achieve various fully heteroatom-substituted P(V) stereocenters from simple POCl 3. Thirteen types of N-, O-, and S-based nucleophiles are adopted for the preparation of six types of P(V) stereocenters. Over 100 examples are provided to show the generality and reliability of the synthetic method. This protocol is also applied to the concise synthesis of twelve bioactive molecules and analogs. The antifungal evaluations of the prepared compounds reveal two new fungicide candidates and also suggest the importance of the stereochemistry for bioactivity.