
Journal of Organic Chemistry p. 4083 - 4088 (1992)
Update date:2022-08-05
Topics:
Posner, Gary H.
Nelson, Todd D.
Kinter, Chris M.
Johnson, Neil
Captodative 3-(tolylthio)-2-pyrone (1) is shown to be reactive as a nucleophilic diene undergoing 2 + 4-cycloadditions with various electrophilic alkenes under sufficiently mild thermal conditions (= 90 deg C) so that the initial bicyclic lactone adducts can be isolated on gram scale in moderate to very good yields (42-82percent) without loss of CO2.These bicyclic adducts are formed regiospecifically and often with excellent stereoselectivity.These Diels-Alder cycloadditions are the first examples of a captodative unsturated sulfide acting as an enophile.NMR data ((13)C) are presented correlating the electron density in the pyrone diene systems with their Diels-Alder reactivity, and some transformations of the bicyclic lactone adducts are shown to illustrate the value and versatility of these richly functionalized synthetic intermediates.
View MoreAllyChem Co., Ltd., Dalian, China(BBChem)
Contact:+86-411-62313318/62313328
Address:No.5 of Jinbin Road, Jinzhou New District, Dalian City, Liaoning Province, P.R.China
website:http://www.mingchem.com/en/index
Contact:0519-85170101-802
Address:Fifth Floor,B of Beihua Buliding,520 Road of Science and Education City,Changwu middle road NO.801,Wujin District,Changzhou,Jiangsu province
HUNAN CHEMAPI BIOLOGICAL TECHNOLOGY CO.,LTD.
Contact:+86-186-02659358
Address:1004, building 3, Wanke Jinsemaitianyuan, 498 Guitang Road, Yuhua District, Changsha City, Hunan Province, China
Tianjin Realet Chemical Technology Co.,Ltd.
website:http://www.realetchem.com
Contact:+86-022-58788819
Address:shuanggang industrial park
RongCheng Tianyu Technology Co.,Ltd.
Contact:86-631-7519595
Address:220Ping Donghai Road RongChengCity,ShangDong Province China
Doi:10.1039/c2ob26614h
(2012)Doi:10.1021/jo302309m
(2013)Doi:10.1016/j.catcom.2012.09.018
(2012)Doi:10.1021/jo402120w
(2013)Doi:10.1002/cbdv.201200308
(2012)Doi:10.1016/j.molstruc.2012.09.078
(2013)