Intramolecular [2+2] Cycloadditions of α-Heteroatom Substituted γ,δ-Unsaturated Ketenes

被引：0
|
作者：
Liu, Tzi-Chi [1 ]
Lin, Zih-Hao [1 ]
Yoo, Woo-Jin [1 ,2 ]
机构：
[1] Natl Taiwan Univ, Dept Chem, 1,Sec 4,Roosevelt Rd, Taipei 10617, Taiwan
[2] Natl Taiwan Univ, Ctr Emerging Mat & Adv Devices, 1,Sec 4,Roosevelt Rd, Taipei 10617, Taiwan
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 13卷 / 10期
关键词：
Cycloaddition; Ketene; Isosteres; Synthetic Methods;
D O I：
10.1002/ajoc.202400302
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An improved synthetic procedure for the intramolecular ketene [2+2] cycloaddition was developed for the preparation of 1-heteroatom-substituted bicyclo[2.1.1]hexan-5-ones. It was found that the use of the Mukaiyama reagent (2-chloro-N-methyl-pyridinium iodide) was key to efficiently generate the alpha-heteroatom substituted homoallyl ketene intermediate for the cycloaddition reaction. The synthetic utility of the resulting bicyclic ketone was demonstrated through the preparation of a saturated variant of vortioxetine. A reliable method for the synthesis of 1-heteroatom-substituted bicyclo[2.1.1]hexan-5-one has been developed through an intramolecular ketene [2+2] cycloaddition reaction. image
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页数：4
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