Copper-Catalyzed α,β-Regioselective (2+4) Cycloaddition of Propargylic Esters

被引:0
|
作者
Zhang, Guo-Ke [1 ]
Wu, Shu-Fang [1 ]
Zhong, Chen [1 ]
Liu, Yu-Qi [1 ]
Wang, Da-Hua [2 ]
Zhang, Yu-Chen [1 ]
Shi, Feng [1 ,3 ,4 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China
[2] Xuzhou Med Univ, Xuzhou Peoples Hosp 1, Xuzhou Municipal Hosp, Dept Otolaryngol, Xuzhou 221002, Jiangsu, Peoples R China
[3] Changzhou Univ, Sch Petrochem Engn, Changzhou 213164, Jiangsu, Peoples R China
[4] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China
关键词
cycloaddition; copper catalysis; phosphorus-containing heterocycles; propargylic esters; regioselectivity; FORMAL 3+2 CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; P(O)H COMPOUNDS; SUBSTITUTION; CYCLIZATION; ALCOHOLS; HYDROPHOSPHORYLATION; ALLENYLATION; CONSTRUCTION;
D O I
10.1002/ejoc.202300802
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed alpha,beta-regioselective (2+4) cycloaddition of propargylic esters with o-hydroxyphenyl substituted secondary phosphine oxides (SPOs) was established, which afforded a series of phosphorus-containing six-membered heterocycles in high yields. This reaction represents the first alpha,beta-regioselective (2+n) cycloaddition of propargylic esters via the intermediates of copper-allenylidenes, which will enrich the chemistry of propargylic esters and copper-allenylidenes. Moreover, this work also represents the first application of o-hydroxyphenyl substituted SPOs as 1,4-dinucleophiles in (2+4) cycloadditions, which provides a useful protocol for the synthesis of phosphorus-containing six-membered heterocycles with potential bioactivity. A copper-catalyzed alpha,beta-regioselective (2+4) cycloaddition of propargylic esters with o-hydroxyphenyl substituted secondary phosphine oxides (SPOs) was established, which afforded phosphorus-containing six-membered heterocycles in high yields. This reaction not only represents the first alpha,beta-regioselective (2+n) cycloaddition of propargylic esters via the intermediates of copper-allenylidenes, but also represents the first application of o-hydroxyphenyl substituted SPOs as 1,4-dinucleophiles in (2+4) cycloadditions.image
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页数:7
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