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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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

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

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