Asymmetric Semipinacol Rearrangement Enabled by Copper-Catalyzed Propargylic Alkylation

被引:14
|
作者
Gong, Fan [1 ]
Meng, Xiangjian [1 ,2 ]
Lan, Shouang [1 ]
Liu, Jinggong [3 ]
Yang, Shuang [1 ]
Fang, Xinqiang [1 ]
机构
[1] Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, State Key Lab Struct Chem, Fuzhou 350100, Peoples R China
[2] Fujian Normal Univ, Coll Chem & Mat Sci, Fuzhou 350007, Peoples R China
[3] Guangdong Prov Hosp Tradit Chinese Med, Orthoped Dept, Guangzhou 510120, Peoples R China
基金
中国国家自然科学基金;
关键词
copper catalysis; propargylic alkylation; semipinacol rearrangement; quaternary stereocenter; cyclopentanone; SEMI-PINACOL REARRANGEMENT; SUBSTITUTION-REACTIONS; ENANTIOSELECTIVE PROPARGYLATION; BETA-KETOESTERS; CARBON CENTERS; ACID; CONSTRUCTION; ALCOHOLS; ESTERS; CYCLOADDITION;
D O I
10.1021/acscatal.2c03623
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The merger of two powerful synthetic strategies, i.e., asymmetric semipinacol-type rearrangement and transition-metal-catalyzed propargylic alkylation, has been achieved, delivering a range of enantioenriched cyclo- and heterocyclopentanones with alpha- alkynylated quaternary stereocenters. Such types of products are challenging to obtain using other methods, and their synthetic value has been demonstrated in a variety of further transformations. The work represents a distinctive mode inducing asymmetric 1,2-carbon migration and further expands the scope of propargylic substitution.
引用
收藏
页码:12036 / 12044
页数:9
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