Journal of Organic Chemistry p. 13691 - 13699 (2018)
Update date:2022-08-04
Topics:
Asahara, Haruyasu
Sofue, Ayano
Kuroda, Yasuyuki
Nishiwaki, Nagatoshi
In the work being reported here, β-nitrostyrenes bearing an ethoxycarbonyl group at the β-position serve as scaffolds for the synthesis of α,β-difunctionalized alkenes. Nitrocinnamates undergo Michael addition reactions with versatile sp3- and sp2-nucleophiles such as alcohols, Grignard reagents, alkylcopper, and dialkylzinc to afford β-substituted nitroethane derivatives. However, various attempts to obtain a double bond via nitrous acid elimination failed because steric repulsion between the newly introduced sp3/sp2 substituent and the nitro group hampered the required anti-coplanar conformation. This problem was successfully overcome using a smaller sp-nucleophile such as lithium acetylide, potassium cyanide, or trimethylsilyl cyanide. While treatment of the adduct with a strong base did not lead to the elimination of nitrous acid, the weaker triethylamine efficiently afforded functionalized enynes and acrylonitriles in high yields.
View MoreNanJing Rate Biochemicals CO., LTD
Contact:+86-25-84931986
Address:NO. 1 Hongjing Road,Jiangning Science Park,Nanjing,China
Shanghai Longjin Metallic Material Co., Ltd.
website:http://www.shlongjin.cn/
Contact:021-56517503,56502257
Address:No.16, Lane 555, Chengyin Road, Shanghai
NEW FORTUNE INDUSTRIAL CO.,LTD.
website:http://newfortune.lookchem.com/
Contact:+86-25-8645-9456
Address:C4-105 GREEN ISLAND FLOWER TOWN
Puyang Huicheng Electronic Material Co., Ltd
website:http://huichengchem.weba.testwebsite.cn/index_en.html
Contact:+86-393-8910800
Address:West Section Shengli Road, Puyang457000, China
Contact:+86-574-87065746
Address:10th Floor, No.787 Baizhang East Road,
Doi:10.3390/molecules25051233
(2020)Doi:10.1021/ol701912s
(2007)Doi:10.1016/j.tetlet.2007.10.147
(2007)Doi:10.1021/ja9097093
(2010)Doi:10.1021/ic101144s
(2010)Doi:10.1021/acs.organomet.0c00013
(2020)