镍催化氟烷基取代的1,6-烯炔的脱氟不对称环化合成司来西坦

doi:10.6023/cjoc202200073

有机化学 ›› 2022, Vol. 42 ›› Issue (12): 4356-4357.DOI: 10.6023/cjoc202200073 上一篇下一篇

所属专题：有机氟化学虚拟合辑；自由基化学专辑

亮点述评

镍催化氟烷基取代的1,6-烯炔的脱氟不对称环化合成司来西坦

林泉^a, 龚和贵^a^,^b^,^*()

a 上海大学材料科学与工程学院上海 200444
b 上海大学化学系超分子化学与催化中心上海 200444

发布日期:2022-12-08
通讯作者: 龚和贵

Nickel-Catalyzed Defluorinative Asymmetric Cyclization of Fluoroalkyl-Substituted 1,6-Enynes for the Synthesis of Seletracetam

Quan Lin^a, Hegui Gong^a^,^b()

a School of Materials Science and Engineering, Shanghai University, Shanghai 200444
b Center for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, Shanghai 200444

Published:2022-12-08
Contact: Hegui Gong

文章分享

摘要/Abstract

引用此文

林泉, 龚和贵. 镍催化氟烷基取代的1,6-烯炔的脱氟不对称环化合成司来西坦[J]. 有机化学, 2022, 42(12): 4356-4357.

Quan Lin, Hegui Gong. Nickel-Catalyzed Defluorinative Asymmetric Cyclization of Fluoroalkyl-Substituted 1,6-Enynes for the Synthesis of Seletracetam[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4356-4357.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 3

图式1. 通过可逆链烯基镍E/Z异构化实现的对映选择性镍催化分子内烯丙基烯基化反应

Scheme 1. Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization

图式2. 反应最优条件和部分实例

Scheme 2. Optimized reaction conditions and selected examples

图式3. 应用于抗癫痫药物司来西坦的对映选择性合成

Scheme 3. Application in the enantioselective synthesis of the antiepileptic drug Seletracetam

参考文献 11

[1]	Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881. doi: 10.1126/science.1131943 pmid: 17901324
[2]	Pollard, J. R. Curr. Opin. Invest. Drugs 2008, 9, 101.
[3]	Lurquin, F.; Driessens, F.; Callaert, M. WO 2005121082, 2005.
[4]	Corpas, J.; Mauleón, P.; Arrayás, R. G.; Carretero, J. C. ACS Catal. 2021, 11, 7513. doi: 10.1021/acscatal.1c01421
[5]	Yap, C.; Lenagh-Snow, G. M. J.; Karad, S. N.; Lewis, W.; Diorazio, L. J.; Lam, H. W. Angew. Chem., Int. Ed. 2017, 56, 8216. doi: 10.1002/anie.201703380
[6]	Wang, K.; Chen, J.; Liu, W.; Kong, W. Angew. Chem., Int. Ed. 2022, e202212664.
[7]	Huang, Y.; Hayashi, T. J. Am. Chem. Soc. 2016, 138, 12340. doi: 10.1021/jacs.6b07844
[8]	Suda, M. Tetrahedron Lett. 1980, 21, 2555. doi: 10.1016/0040-4039(80)80127-4
[9]	Wang, B.; Zhao, X.; Liu, Q.; Cao, S. Org. Biomol. Chem. 2018, 16, 8546. doi: 10.1039/C8OB02322K
[10]	Pichon, M. M.; Stauffert, F.; Addante-Moya, L. G.; Bodlenner, A.; Compain, P. Eur. J. Org. Chem. 2018, 1538.
[11]	Lin, Q.; Xu, X.; Qing, F. Org. Biomol. Chem. 2015, 13, 8740. doi: 10.1039/c5ob01302j pmid: 26185911

镍催化氟烷基取代的1,6-烯炔的脱氟不对称环化合成司来西坦

Nickel-Catalyzed Defluorinative Asymmetric Cyclization of Fluoroalkyl-Substituted 1,6-Enynes for the Synthesis of Seletracetam

RichHTML

PDF

可视化

摘要/Abstract

引用此文

分享此文

图/表 3

参考文献 11

相关文章 0

编辑推荐

相关统计

本文评价