
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 MoreJiangxi Province Bethel Pharmaceutical Co., Ltd.
Contact:+86-795-259 3456 ,+86-15957688008 13566650571
Address:Huangjindui Chemical Park, Shanggao County ,Yichun city,Jiangxi Province
website:http://www.maisonchem.com.cn
Contact:0086-311-83833777
Address:Leitou industrial district, xinji, shijiazhuang city, hebei province,
Contact:13813902930 025-52714267
Address:20 Fengji Road, Yuhua Economic Development Zone, Nanjing, Jiangsu, P. R. China
Shenzhen Sunrising Industry Co., ltd.
Contact:+86 755 86571158 / 86571159 / 86571160
Address:2108 ZHENYE INT. BUSINESS CENTER,NO.3101-90 QIANHAI RD, NANSHAN,SHENZHEN, CHINA
JiangXi Keyuan Biopharma Co., LTD.
Contact:+86-563-6833666
Address:Guangde Fine Chemical Zone, Anhui 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)