Journal of the American Chemical Society p. 9515 - 9518 (2017)
Update date:2022-07-29
Topics: Aerobic Copper-Catalyzed Direct synthesis
Wdowik, Tomasz
Chemler, Sherry R.
A new method for the direct conversion of 4-pentenylsulfonamides to 2-formylpyrrolidines and a 2-ketopyrrolidine has been developed. This transformation occurs via aerobic copper-catalyzed alkene aminooxygenation where molecular oxygen serves as both oxidant and oxygen source. The 2-formylpyrrolidines can further undergo oxidative carbon-carbon bond cleavage in situ upon addition of DABCO, providing 2-pyrrolidinones. These transformations have been demonstrated for a range of 4-pentenylsulfonamides. 4-Pentenylalcohols also undergo oxidative cyclization to form γ-lactones predominantly. The reaction is chemoselective, oxidizing one alkene in the presence of others, and is compatible with several functional groups. Application of these reactions to the formal syntheses of baclofen and (+)-monomorine was demonstrated.
View MoreContact:+86-025-52406782
Address:8 Taizishan Rd., Yanjiang Industrial Development Area, Nanjing, Jiangsu, China.
Tianjin Boron PharmaTech Co.,Ltd.(expird)
Contact:86-022-59845187
Address:B9-401, Tianda Science Park,No.80,4th Avenue,TEDA,Tianjin, China
Suzhou Jingye Medicine & Chemical Co., Ltd
website:http://www.jingyechem.cn
Contact:+86-512-66658588
Address:No. 88, Sanlian Street, Jinfeng Road, Suzhou New District, Jiangsu Province, P. R. China
shijiazhuang shuanglian chemical industry co.,ltd
Contact:0311-82190302
Address:Luquan Intersection , Shijiazhuang--Taiyuan Expressway,Shijiazhuang City
Engineering Research Center of Pesticide, Heilongjiang Province
Contact:+86-451-86609001
Address:No.74 of Xuefu Road, Nangang District,
Doi:10.1016/j.tet.2011.05.121
(2011)Doi:10.1021/ol201812n
(2011)Doi:10.1021/jm200734j
(2011)Doi:10.1021/ma201280s
(2011)Doi:10.1016/S0040-4039(00)97262-9
(1990)Doi:10.1021/j100160a007
(1991)