The sequential C–H oxidation/asymmetric phosphonylation of primary alcohols to synthesize α-hydroxy phosphonates
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 alcoho...
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2021-08-01
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doaj-fb7509e1b4d04d2aae25a22eab54adec2021-10-05T04:21:44ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492021-08-0123315319The sequential C–H oxidation/asymmetric phosphonylation of primary alcohols to synthesize α-hydroxy phosphonatesShifu Ying0Xiaoling Huang1Xinwei Guo2Shangdong Yang3State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, ChinaState Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, ChinaState Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, ChinaState 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, ChinaA 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.http://www.sciencedirect.com/science/article/pii/S2666554921000570Hiral α-hydroxy phosphonates: primary alcohols: Cu(I)/TEMPO/NMIAl(salalen): C–H oxidation |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Shifu Ying Xiaoling Huang Xinwei Guo Shangdong Yang |
spellingShingle |
Shifu Ying Xiaoling Huang Xinwei Guo Shangdong Yang The sequential C–H oxidation/asymmetric phosphonylation of primary alcohols to synthesize α-hydroxy phosphonates Green Synthesis and Catalysis Hiral α-hydroxy phosphonates: primary alcohols: Cu(I)/TEMPO/NMI Al(salalen): C–H oxidation |
author_facet |
Shifu Ying Xiaoling Huang Xinwei Guo Shangdong Yang |
author_sort |
Shifu Ying |
title |
The sequential C–H oxidation/asymmetric phosphonylation of primary alcohols to synthesize α-hydroxy phosphonates |
title_short |
The sequential C–H oxidation/asymmetric phosphonylation of primary alcohols to synthesize α-hydroxy phosphonates |
title_full |
The sequential C–H oxidation/asymmetric phosphonylation of primary alcohols to synthesize α-hydroxy phosphonates |
title_fullStr |
The sequential C–H oxidation/asymmetric phosphonylation of primary alcohols to synthesize α-hydroxy phosphonates |
title_full_unstemmed |
The sequential C–H oxidation/asymmetric phosphonylation of primary alcohols to synthesize α-hydroxy phosphonates |
title_sort |
sequential c–h oxidation/asymmetric phosphonylation of primary alcohols to synthesize α-hydroxy phosphonates |
publisher |
KeAi Communications Co. Ltd. |
series |
Green Synthesis and Catalysis |
issn |
2666-5549 |
publishDate |
2021-08-01 |
description |
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. |
topic |
Hiral α-hydroxy phosphonates: primary alcohols: Cu(I)/TEMPO/NMI Al(salalen): C–H oxidation |
url |
http://www.sciencedirect.com/science/article/pii/S2666554921000570 |
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