The sequential C–H oxidation/asymmetric phosphonylation of primary alcohols to synthesize α-hydroxy phosphonates

• Main Authors: Shifu Ying, Xiaoling Huang, Xinwei Guo, Shangdong Yang
• Format: Article
• Language: English
• Published: KeAi Communications Co. Ltd. 2021-08-01
• Series: Green Synthesis and Catalysis
• Subjects: Hiral α-hydroxy phosphonates: primary alcohols: Cu(I)/TEMPO/NMI; Al(salalen): C–H oxidation
• Online Access: http://www.sciencedirect.com/science/article/pii/S2666554921000570
• ISSN: 2666-5549

A new strategy for the sequential C–H oxidation/asymmetric phosphonylation of primary alcohols has been developed. It involves a combination of Cu(I)/TEMPO/NMI (N-methylimidazole) oxidation, under an air atmosphere, with chiral Al (salalen)-catalyzed enantioselective addition. Various primary alcohols, including benzylic alcohols, allylic alcohols, propargylic alcohols, alkyl alcohols, and other alcohols containing oxygen-, sulfur-, and nitrogen-heterocycles were smoothly converted into chiral α-hydroxy phosphonates with good yields and high enantioselectivities. Inhibitor of CD45 and a plant growth regulator can be easily synthesized by this new method.