Enantioselective synthesis of chiral phosphonylated 2,3-dihydrofurans by copper catalyzed asymmetric formal [3+2] cycloaddition of propargylic esters with β-keto phosphonates

doi:10.1016/S1872-2067(16)62488-9

Chinese Journal of Catalysis ›› 2016, Vol. 37 ›› Issue (8): 1389-1395.DOI: 10.1016/S1872-2067(16)62488-9

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Enantioselective synthesis of chiral phosphonylated 2,3-dihydrofurans by copper catalyzed asymmetric formal [3+2] cycloaddition of propargylic esters with β-keto phosphonates

Xiushuai Chen^a,b, Chuanjin Hou^a, Qing Li^a,b, Yanjun Liu^a, Ruifeng Yang^a, Xiangping Hu^b

a. School of Light Industry and Chemical Engineering, Dalian Polytechnic University, Dalian 116034, Liaoning, China;
b. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received:2016-05-21 Revised:2016-06-14 Online:2016-07-29 Published:2016-08-01
Contact: Chuanjin Hou, Yanjun Liu, Xiangping Hu
Supported by:
This work was supported by the National Natural Science Foundation of China (21403022, 21572226) and the Natural Science Foundation of Liaoning Province of China (2015020194).

Abstract

Abstract:

Copper catalyzed asymmetric formal [3+2] cycloaddition of propargylic esters to β-keto phosphonates for the synthesis of chiral phosphonylated 2,3-dihydrofurans was developed. By using a bulky and structurally rigid tridentate ketimine P,N,N ligand, a series of optically active phosphonylated 2,3-dihydrofurans were prepared in high yield and up to 92% ee.

Key words: Copper, Asymmetric synthesis, [3+2] Cycloaddition, β-Keto phosphonates, Phosphonylated 2,3-dihydrofurans

Xiushuai Chen, Chuanjin Hou, Qing Li, Yanjun Liu, Ruifeng Yang, Xiangping Hu. Enantioselective synthesis of chiral phosphonylated 2,3-dihydrofurans by copper catalyzed asymmetric formal [3+2] cycloaddition of propargylic esters with β-keto phosphonates[J]. Chinese Journal of Catalysis, 2016, 37(8): 1389-1395.

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Enantioselective synthesis of chiral phosphonylated 2,3-dihydrofurans by copper catalyzed asymmetric formal [3+2] cycloaddition of propargylic esters with β-keto phosphonates

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