Chemical Science p. 774 - 779 (2021)
Update date:2022-07-30
Topics:
Ma, Liang
Kou, Luyao
Jin, Feng
Cheng, Xionglve
Tao, Suyan
Jiang, Gangzhong
Bao, Xiaoguang
Wan, Xiaobing
We report the first demonstrations of intra- and intermolecular acyclic nitronate olefin cycloaddition (ANOC) reactions that enable the highly efficient syntheses of isoxazolines bearing various functional groups. This general approach to accessing γ-lactone fused isoxazolines was hitherto unprecedented. The room temperature transformations reported herein exhibit wide substrate scopes, as evidenced by more than 70 examples, including the generation of five tricyclic isoxazolines. The robustness of this methodology was confirmed by a series of trials that afforded highly functionalized isoxazolines. Both experimental results and density functional theory calculations indicate that these transformations proceed via the in situ formation of acyclic nitronates together with concerted [3+2] cycloaddition and tert-butyloxy group elimination processes to give regio- and stereospecificity. This journal is
View MoreChangzhou Welton Chemical Co., Ltd,
Contact:0086-519-85910828,85920537,85912897
Address:No.8 Jinlong Road, Binjiang Park, Changzhou, Jiangsu, China.
Shenzhen JYMed Technology Co.,Ltd.
website:http://www.jymedtech.com
Contact:+86-755-26612112
Address:1#8,9/F, Biomedicine innovation Industrial Park, No.14, Jinhui Road, Pingshan Sistrict, Shenzhen, China
Hangzhou Deli Chemical Co.,Ltd.
website:http://www.dlchemical.com
Contact:86 571 28006267
Address:Tangxi Industrial Area, Yuhang District, Hangzhou
website:http://www.weichichem.com
Contact:+8613912949432
Address:Fine Chemical Industrial Base,Wujiang town,He County,Anhui China.
Jinan Jinguilin Chemical Co.,Ltd
Contact:+86-531-81188412
Address:3rd floor of Torch Building, Huanyuan Rd, City of Jinan
Doi:10.1039/b912721f
(2010)Doi:10.1002/chem.200901307
(2009)Doi:10.1021/ol9025777
(2010)Doi:10.1134/S1070328409030099
(2009)Doi:10.1002/anie.201709511
(2017)Doi:10.1021/ol902920u
(2010)