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
来源：
ORGANOMETALLICS | 2021年 / 40卷 / 03期
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
  • [31] Pd-catalyzed decarboxylative couplings of arenecarboxylic acids with aryl iodides
    Wang, Zhiyong
    Ding, Qiuping
    He, Xiaodan
    Wu, Jie
    [J]. TETRAHEDRON, 2009, 65 (24) : 4635 - 4638
  • [32] Highly Enantioselective Synthesis of Sultams via Pd-Catalyzed Hydrogenation
    Yu, Chang-Bin
    Wang, Da-Wei
    Zhou, Yong-Gui
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15): : 5633 - 5635
  • [33] Development of and Recent Advances in Pd-Catalyzed Decarboxylative Asymmetric Protonation
    Kingston, Cian
    James, Jinju
    Guiry, Patrick J.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (02): : 473 - 485
  • [34] A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes
    Hou, Chuan-Jin
    Schuppe, Alexander W.
    Knippel, James Levi
    Ni, Anton Z.
    Buchwald, Stephen L.
    [J]. ORGANIC LETTERS, 2021, 23 (22) : 8816 - 8821
  • [35] Rhodium-Catalyzed Decarboxylative Cycloaddition Route to Substituted Anilines
    Zhang, Kainan
    Louie, Janis
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (11): : 4686 - 4691
  • [36] Recent Advances in the Synthesis of α-Alkylidene-Substituted δ-Lactones, γ-Lactams and δ-Lactams
    Albrecht, Anna
    Albrecht, Lukasz
    Janecki, Tomasz
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (15) : 2747 - 2766
  • [37] Reaction development of Pd-catalyzed synthesis of substituted 2-pyridones
    McLernon, Bailey
    Waetzig, Shelli
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [38] Pd-Catalyzed Cascade Reaction for the Synthesis of 2-Substituted Indoles
    Jadhav, Jagannath
    Gaikwad, Vipul
    Kurane, Rajanikant
    Salunkhe, Rajashri
    Rashinkar, Gajanan
    [J]. SYNLETT, 2012, (17) : 2511 - 2515
  • [39] Ni- and Pd-Catalyzed Synthesis of Substituted and Functionalized Allylic Boronates
    Zhang, Ping
    Roundtree, Ian A.
    Morken, James P.
    [J]. ORGANIC LETTERS, 2012, 14 (06) : 1416 - 1419
  • [40] Synthesis of substituted oxazoles via Pd-catalyzed tandem oxidative cyclization
    Zhang, Wei
    Yu, Wenlong
    Yan, Qiangqiang
    Liu, Zhanxiang
    Zhang, Yuhong
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (12): : 2428 - 2432
12345