Pd-Catalyzed Decarboxylative Cycloaddition for the Synthesis of Highly Substituted δ-Lactones and Lactams

被引:7
|
作者
Shi, Linlin [1 ,2 ]
He, Yingdong [1 ]
Gong, Jianxian [1 ]
Yang, Zhen [1 ,3 ,4 ,5 ]
机构
[1] Peking Univ, State Key Lab Chem Oncogen, Key Lab Chem Genom, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
[2] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Henan, Peoples R China
[3] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China
[4] Peking Univ, Beijing Natl Lab Mol Sci BNLMS, Beijing 100871, Peoples R China
[5] Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China
基金
美国国家科学基金会;
关键词
Catalytic system - Cyclic carbonates - Cycloaddition process - Double bonds - Palladium-catalyzed - Regio-selective - Situ generation;
D O I
10.1021/acs.organomet.0c00646
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An efficient palladium-catalyzed decarboxylative cycloaddition process of vinyl cyclic carbonates and vinyl-oxazolidinones for the synthesis of highly substituted delta-lactone and delta-lactam derivatives was developed. This protocol exhibits several unique characteristics, including broad substrate scope, good functional group tolerance, and operational convenience, which enables a regioselective access to a variety of lactone and lactam scaffolds in moderate to good yield. The redox-neutral catalytic system promotes formation of substituted scaffolds with in situ generation of a cyclic tetra-substituted double bond functionality.
引用
收藏
页码:324 / 332
页数:9
相关论文
共 50 条
  • [1] Synthesis of γ-Lactams and γ-Lactones via Intramolecular Pd-Catalyzed Allylic Alkylations
    Kammerer, Claire
    Prestat, Guillaume
    Madec, David
    Poli, Giovanni
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (12) : 3439 - 3447
  • [2] Pd-Catalyzed Decarboxylative Cycloaddition of Vinylethylene Carbonates with Isothiocyanates
    Xiong, Wei
    Zhang, Shengjun
    Li, Huijun
    Zhang, Zhifeng
    Xu, Tongyu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (14): : 8773 - 8779
  • [3] Synthesis of Substituted γ- and δ-Lactams via Pd-Catalyzed Alkene Carboamination Reactions
    Boothe, Jordan R.
    Shen, Yifan
    Wolfe, John P.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (05): : 2777 - 2786
  • [4] Pd-Catalyzed Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Imines
    Yang, Lei
    Khan, Ajmal
    Zheng, Renfeng
    Jin, Long Yi
    Zhang, Yong Jian
    [J]. ORGANIC LETTERS, 2015, 17 (24) : 6230 - 6233
  • [5] Synthesis of Biaryls by Pd-Catalyzed Decarboxylative Homo- and Heterocoupling of Substituted Benzoic Acids
    Xie, Kai
    Wang, Sizhuo
    Yang, Zhiyong
    Liu, Jidan
    Wang, Anwei
    Li, Xiujian
    Tan, Ze
    Guo, Can-Cheng
    Deng, Wei
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (29) : 5787 - 5790
  • [6] Pd-Catalyzed Decarboxylative Asymmetric Protonation of Sterically Hindered -Aryl Lactones and Dihydrocoumarins
    James, Jinju
    Akula, Ramulu
    Guiry, Patrick J.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (16) : 3138 - 3149
  • [7] Pd-Catalyzed asymmetric decarboxylative cycloaddition of vinylethylene carbonates with 3-cyanochromones
    Khan, Ijaz
    Zhao, Can
    Zhang, Yong Jian
    [J]. CHEMICAL COMMUNICATIONS, 2018, 54 (37) : 4708 - 4711
  • [8] Expedient synthesis of 3-substituted cycloalkanones via a Pd-catalyzed decarboxylative protonation protocol
    Kim, Se Hee
    Kim, Eun Sun
    Kim, Taek Hyeon
    Kim, Jae Nyoung
    [J]. TETRAHEDRON LETTERS, 2009, 50 (46) : 6256 - 6260
  • [9] SYNTHESIS OF BIARYLS VIA Pd-CATALYZED DECARBOXYLATIVE COUPLING OF SUBSTITUTED BENZOIC ACIDS WITH PHENYLBORONIC ACIDS
    Wang, Anwei
    Li, Xiujian
    Liu, Jidan
    Gui, Qingwen
    Chen, Xiang
    Tan, Ze
    Xie, Kai
    [J]. SYNTHETIC COMMUNICATIONS, 2014, 44 (02) : 289 - 295
  • [10] Synthesis of α,β-Unsaturated Ketones by Pd-Catalyzed Decarboxylative Allylation of α-Oxocarboxylates
    Rodriguez, Nuria
    Manjolinho, Filipe
    Gruenberg, Matthias F.
    Goossen, Lukas J.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (49) : 13688 - 13691