Synthesis of spiro 1,3-oxazolidines via palladium-catalyzed [3+2] cycloaddition of vinyl epoxides with cyclohexadienimines

被引：4
|
作者：
Qin, Shaoheng [1 ]
He, Qiuqin [2 ]
Wang, Jingyun [1 ]
Zhou, Ming-Dong [1 ]
机构：
[1] Liaoning Shihua Univ, Sch Chem & Mat Sci, 1 Dandong Rd, Fushun 113001, Peoples R China
[2] Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China
来源：
JOURNAL OF SAUDI CHEMICAL SOCIETY | 2020年 / 24卷 / 06期
关键词：
Spiro 1,3-oxazolidine; Palladium-catalyzed; Cycloaddition; ENANTIOSELECTIVE SYNTHESIS; VINYLOXIRANES; OXIRANES; ROUTE; CONSTRUCTION; DERIVATIVES; ACTIVATION; IMINES;
D O I：
10.1016/j.jscs.2020.03.008
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A palladium-catalyzed chemoselective [3 + 2] cycloaddition of vinyl epoxide with cyclohexadienimines was developed. The reaction gave rise to a range of spiro 1,3-oxazolidines in moderate to good yields. (C) 2020 Published by Elsevier B.V. on behalf of King Saud University.
引用
收藏
页码：445 / 450
页数：6
相关论文
共 50 条
  • [1] A new synthetic route to 1,3-oxazolidines via palladium-catalyzed regioselective [3+2] cycloaddition of vinylic oxiranes with imines
    Shim, JG
    Yamamoto, Y
    HETEROCYCLES, 2000, 52 (02) : 885 - 895
  • [2] Cation radical [3+2] cycloaddition of chalcone epoxides (II): A facile synthesis of highly substituted 1,3-oxazolidines
    Huo, CD
    Wei, R
    Zhang, W
    Yang, L
    Liu, ZL
    SYNLETT, 2005, (01) : 161 - 163
  • [3] Asymmetric Synthesis of N-Fused 1,3-Oxazolidines via Pd-Catalyzed Decarboxylative (3+2) Cycloaddition
    Park, Jong-Un
    Ahn, Hye-In
    Cho, Ho-Jun
    Xuan, Zi
    Kim, Ju Hyun
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (09) : 1836 - 1840
  • [4] Highly Stereoselective Palladium-Catalyzed [3+2] Cycloaddition of Vinyl Epoxides and N-Benzothiazolimines
    Song, Xiaoxiao
    Gu, Mengjie
    Chen, Xiaoyun
    Xu, Lei
    Ni, Qijian
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (12) : 2180 - 2183
  • [5] Ytterbium(III) triflate catalyzed [3+2] cycloaddition of N-arylimines and epoxides:: A novel and solvent-free synthesis of substituted 1,3-oxazolidines
    Yu, Chuanming
    Dai, Xiaoping
    Su, Weike
    SYNLETT, 2007, (04) : 646 - 648
  • [6] Highly Diastereo- and Enantioselective Palladium-Catalyzed [3+2] Cycloaddition of Vinyl Epoxides and α,β-Unsaturated Ketones
    Suo, Jia-Jia
    Du, Juan
    Liu, Qing-Rong
    Chen, Di
    Ding, Chang-Hua
    Peng, Qian
    Hou, Xue-Long
    ORGANIC LETTERS, 2017, 19 (24) : 6658 - 6661
  • [7] Synthesis of 1,3-oxazolidines from imines and epoxides catalyzed by samarium compounds
    Nishitani, T
    Shiraishi, H
    Sakaguchi, S
    Ishii, Y
    TETRAHEDRON LETTERS, 2000, 41 (18) : 3389 - 3393
  • [8] Enantioselective Formal [3+2] Cycloaddition of Epoxides with Imines under BrOnsted Base Catalysis: Synthesis of 1,3-Oxazolidines with Quaternary Stereogenic Center
    Kondoh, Azusa
    Akahira, Shiori
    Oishi, Masafumi
    Terada, Masahiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (21) : 6299 - 6303
  • [9] Diastereoselective Synthesis of 1,3-Oxazolidines via Cationic Iron Porphyrin-catalyzed Cycloaddition of Aziridines with Aldehydes
    Teranishi, Satoru
    Maeda, Kazuki
    Kurahashi, Takuya
    Matsubara, Seijiro
    ORGANIC LETTERS, 2019, 21 (08) : 2593 - 2596
  • [10] Palladium-Catalyzed Formal (3+2) Cycloaddition Reactions of 2-Nitro-1,3-enynes with Vinylaziridines, -epoxides, and -cyclopropanes
    Drew, Melanie A.
    Tague, Andrew J.
    Richardson, Christopher
    Pyne, Stephen G.
    Hyland, Christopher J. T.
    ORGANIC LETTERS, 2021, 23 (12) : 4635 - 4639
12345