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

Shifu Ying; Xiaoling Huang; Xinwei Guo; Shangdong Yang

Green Synthesis and Catalysis (Aug 2021)

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

Shifu Ying,
Xiaoling Huang,
Xinwei Guo,
Shangdong Yang

Affiliations

Shifu Ying: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
Xiaoling Huang: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
Xinwei Guo: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
Shangdong Yang: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China; State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Lanzhou 730000, China; Corresponding author. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

Journal volume & issue: Vol. 2, no. 3
pp. 315 – 319

Abstract

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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.

Published in Green Synthesis and Catalysis

ISSN: 2666-5549 (Online)
Publisher: KeAi Communications Co. Ltd.
Country of publisher: China
LCC subjects: Technology: Chemical technology; Science: Chemistry: Organic chemistry: Biochemistry
Website: https://www.keaipublishing.com/en/journals/green-synthesis-and-catalysis/

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