Tetrahedron p. 5883 - 5900 (1992)
Update date:2022-08-04
Topics:
Celli, Angela M.
Scotton, Mirella
Sega, Alessandro
The hetero-Diels-Alder reaction of 1-oxabutadienes 1a-c bearing electron-withdrawing groups with ethyl vinyl ether and 2,3-dihydrofuran gave the functionalized 5,6-dihydro-4H-pyrans 2a-c, 4c and 4H-4a,5,6,6a-tetrahydrofuro<2,3-b>pyrans 5a-c and 6c.Cycloadducts 2a and 4c easily rearranged to furo<2,3-b>furans 3a, 3c and 9c and cycloadducts 5a and 6c to difuro<2,3-b:3',4'-d>furans 7a, 7c and 8c.The stereochemistry of the compounds 5c and 7a was determined by single crystal X-ray analysis.Relative configurations of the other compounds were established by nOe data.Some aspects of the reaction mechanisms are discussed. Key Words: furo-furans, furo-pyrans, hetero-Diels-Alder, nOes.
View MoreContact:+86-13914766747
Address:Floors 21&22, Jin Cheng Tower, No. 216 Middle Longpan Road, Nanjing
Jiaozuo Zhongwen Trading Coporation Limited
Contact:+86 0391-3553810
Address:East Renmin Road
Nanjing Samwon International Limited
Contact:+86-25-84873444
Address:1108, BLDG B, New Century Plaza, No 1, South Taiping Rd.,
Qingdao Kingway Pharmtech Co., Ltd.
Contact:86-532-87118899
Address:No. 88, Middle Haixi Road, Jiaonan City, Qingdao, China
Zhangjiagang Golden Reach Fine Chemical Co.,LTD.
Contact:+86-512-6585 6968
Address:Changfu Road， Dongsha Chemical Industry Park, Zhangjiagang City, Jiangsu Province, China
Doi:10.1016/S0040-4020(01)86311-0
(1993)Doi:10.1021/jo400342y
(2013)Doi:10.1016/j.tet.2013.03.052
(2013)Doi:10.1016/j.catcom.2013.03.012
(2013)Doi:10.1016/j.tet.2013.03.059
(2013)Doi:10.1016/S0040-4039(00)92532-2
(1992)
