Synthesis of 5-Vinyl-2-isoxazolines by Palladium-Catalyzed Intramolecular O-Allylation of Ketoximes

被引：12
|
作者：
Fernandes, Rodney A. [1 ]
Gangani, Ashvin J. [1 ]
Panja, Arpita [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 16期
关键词：
ALLYLIC SUBSTITUTION; ISOXAZOLINE; DERIVATIVES; MIGRATION; LIGAND; ACIDS;
D O I：
10.1021/acs.orglett.1c01897
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the synthesis of 5-vinyl-2-isoxazolines by Pd-catalyzed intramolecular O-allylation of ketoximes has been developed. The reaction involves Pd(0)-catalyzed p-allyl formation via leaving group ionization or Pd(II)-catalyzed allylic C-H activation followed by intramolecular nucleophilic oxime oxygen attack. This methodology has been elaborated to various value-added products by epoxidation, Wacker oxidation, cross-metathesis, hydroboration-oxidation, dihydroxylation, and catalytic hydrogenation.
引用
收藏
页码：6227 / 6231
页数：5
相关论文
共 50 条
  • [41] PALLADIUM-CATALYZED ALLYLATION OF 5-MEMBERED HETEROCYCLIC AMBIDENT SULFUR NUCLEOPHILES
    ARREDONDO, Y
    MORENOMANAS, M
    PLEIXATS, R
    VILLARROYA, M
    TETRAHEDRON, 1993, 49 (07) : 1465 - 1470
  • [42] Asymmetric Formal Synthesis of (-)-Cephalotaxine via Palladium-Catalyzed Enantioselective Tsuji Allylation
    Zhang, Zhi-Wei
    Wang, Cui-Cui
    Xue, Hong
    Dong, Yu
    Yang, Jian-Hua
    Liu, Shouxin
    Liu, Wen-Qing
    Li, Wei-Dong Z.
    ORGANIC LETTERS, 2018, 20 (04) : 1050 - 1053
  • [43] Palladium-catalyzed allylation and deacylative allylation of 3-acetyl-2-oxindoles with allylic alcohols
    Ortega-Martinez, Aitor
    de Lorenzo, Rocco
    Sansano, Jose M.
    Najera, Carmen
    TETRAHEDRON, 2018, 74 (02) : 253 - 259
  • [44] Palladium-catalyzed carbonyl allylation of aldehydes with allylic phosphates: Synthesis of homoallylic alcohols
    Kang, SK
    Kim, DY
    Hong, RK
    Ho, PS
    SYNTHETIC COMMUNICATIONS, 1996, 26 (08) : 1493 - 1498
  • [45] Enantioselective Palladium-Catalyzed Decarboxylative Allylation of Carbazolones: Total Synthesis of (-)-Aspidospermidine and (+)-Kopsihainanine A
    Li, Zeqian
    Zhang, Shaoxiong
    Wu, Shoutao
    Shen, Xiaolei
    Zou, Liwei
    Wang, Fengqun
    Li, Xiang
    Peng, Fangzhi
    Zhang, Hongbin
    Shao, Zhihui
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (15) : 4117 - 4121
  • [46] Palladium-Catalyzed Oxidative Allylation of Sulfoxonium Ylides: Regioselective Synthesis of Conjugated Dienones
    Li, Chunsheng
    Li, Meng
    Zhong, Wentao
    Jin, Yangbin
    Li, Jianxiao
    Wu, Wanqing
    Jiang, Huanfeng
    ORGANIC LETTERS, 2019, 21 (04) : 872 - 875
  • [47] Palladium-Catalyzed Carbonyl Allylation: Synthesis of Enantiomerically Pure α-Substituted Allylboronic Esters
    Fernandez, Enrique
    Pietruszka, Joerg
    SYNLETT, 2009, (09) : 1474 - 1476
  • [48] Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation
    Vita, Maria Victoria
    Caramenti, Paola
    Waser, Jerome
    ORGANIC LETTERS, 2015, 17 (23) : 5832 - 5835
  • [49] Enantioselective Palladium-Catalyzed Decarboxylative Allylation of Carbazolones and Indolones: Formal Synthesis of (+)-KopsihainanineA
    Gartshore, Christopher J.
    Lupton, David W.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (15) : 4113 - 4116
  • [50] Palladium-catalyzed intramolecular C-O bond formation: An approach to the synthesis of chiral benzodioxocines
    Neogi, Arpita
    Majhi, Tirtha P.
    Achari, Basudeb
    Chattopadhyay, Partha
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (02) : 330 - 336
12345