Palladium-catalyzed stereoselective (3+2) cycloaddition of vinylethylene carbonates with cyclic N-sulfonyl ketimines

被引：13
作者：
Gao, Xing [1 ,2 ]
Zhu, Dongyu [1 ,2 ]
Jiang, Feng [1 ,2 ]
Liao, Jianning [1 ,2 ]
Wang, Wei [3 ]
Wu, Yongjun [3 ]
Zheng, Lufei [4 ]
Guo, Hongchao [1 ,2 ,5 ]
机构：
[1] China Agr Univ, Dept Chem, Beijing 100193, Peoples R China
[2] China Agr Univ, Innovat Ctr Pesticide Res, Beijing 100193, Peoples R China
[3] Zhengzhou Univ, Coll Publ Hlth, Zhengzhou 450001, Peoples R China
[4] Chinese Acad Agr Sci, Inst Qual Stand & Testing Technol Agroprod, Beijing 100081, Peoples R China
[5] China Agr Univ, Dept Nutr & Hlth, Beijing 100193, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 22期
基金：
中国国家自然科学基金;
关键词：
DECARBOXYLATIVE CYCLOADDITION; ENANTIOSELECTIVE CONSTRUCTION; AZOMETHINE YLIDES; TERTIARY; ACCESS; FERMENTATION; HETEROCYCLES; SPIROKETALS; ALLYLATION; ANNULATION;
D O I：
10.1039/d1ob00614b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A diastereoselective (3 + 2) cycloaddition of N-sulfonyl ketimines with vinylethylene carbonates (VECs) in the presence of Pd(2)dba(3)center dot CHCl3 and PPh3 has been developed. The reaction of various substituted VECs and diverse cyclic N-sulfonyl ketimines proceeded smoothly under mild conditions, giving highly functionalized oxazolidine frameworks in good to excellent yields with moderate to good diastereoselectivities. With the use of spiroketal-based diphosphine SKP as a chiral ligand, an asymmetric version of the current (3 + 2) cycloaddition was achieved, and chiral products were obtained in >99% ee in most cases.
引用
收藏
页码：4877 / 4881
页数：5
相关论文
共 50 条
  • [31] PdII-Catalyzed Spiroannulation of Cyclic N-Sulfonyl Ketimines with Aryl Iodides through C-H Bond Activation
    Reddy, K. Nagarjuna
    Rao, M. V. Krishna
    Sridhar, B.
    Reddy, B. V. Subba
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (28) : 4085 - 4090
  • [32] Rhodium-catalyzed addition reactions of benzylic C-H bonds to cyclic N-sulfonyl ketimines via π-coordination
    Li, Yuntong
    Shi, Hang
    CHINESE CHEMICAL LETTERS, 2024, 35 (03)
  • [33] Highly Diastereo- and Enantioselective Palladium-Catalyzed [3+2] Cycloaddition of Vinyl Aziridines and α,β-Unsaturated Ketones
    Xu, Chao-Fan
    Zheng, Bao-Hui
    Suo, Jia-Jia
    Ding, Chang-Hua
    Hou, Xue-Long
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (05) : 1604 - 1607
  • [34] Rapid Access to Spirocyclic Oxindole Alkaloids: Application of the Asymmetric Palladium-Catalyzed [3+2] Trimethylenemethane Cycloaddition
    Trost, Barry M.
    Bringley, Dustin A.
    Zhang, Ting
    Cramer, Nicolai
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (44) : 16720 - 16735
  • [35] Palladium-Catalyzed Asymmetric [3+2] Cycloaddition Reaction of Vinyl Cyclopropane with Electron-Deficient Dienes
    Li, Yun-Fan
    Yang, Cun
    Xi, Yu-Ting
    Tan, Qitao
    Ding, Chang-Hua
    Xu, Bin
    SYNLETT, 2024, 35 (18) : 2101 - 2106
  • [36] Asymmetric Synthesis of Methylenetetrahydrofurans by Palladium-Catalyzed [3+2] Cycloaddition of Trimethylenemethane with Aldehydes - A Novel Ligand Design
    Trost, Barry M.
    Bringley, Dustin A.
    Silverman, Steven M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (20) : 7664 - 7667
  • [37] Dearomatization of 3-Nitroindoles Enabled Using Palladium-Catalyzed Decarboxylative [4+2] Cycloaddition of2-Alkylidenetrimethylene Carbonates
    Dou, Pei-Hao
    Yuan, Shu-Pei
    Chen, Yan
    Zhao, Jian-Qiang
    Wang, Zhen-Hua
    You, Yong
    Zhang, Yan-Ping
    Zhou, Ming-Qiang
    Yuan, Wei-Cheng
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (09) : 6025 - 6037
  • [38] Synthesis of Tetrasubstituted Furans by Palladium-Catalyzed Decarboxylative [3+2] Cyclization of Propargyl β-Keto Esters
    Yoshida, Masahiro
    Ohno, Shoko
    Shishido, Kozo
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (06) : 1604 - 1607
  • [39] Synthesis of Polycyclic Imidazolidinones via Cascade [3+2]-Annulation of β-Oxo-acrylamides with Cyclic N-Sulfonyl Imines
    Xie, Lei
    Zhao, Chenyi
    Wang, Zhaoxue
    Chen, Zirui
    Zhao, Yingying
    Liu, Xinghan
    Xu, Xiangdong
    Liu, Wanxing
    Li, Xiaojing
    Wu, Lingang
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (22) : 15805 - 15816
  • [40] Asymmetric Synthesis of 3,4-Dihydroquinolin-2-ones via a Stereoselective Palladium-Catalyzed Decarboxylative [4+2]-Cycloaddition
    Jin, Jing-Hai
    Wang, Hao
    Yang, Zhong-Tao
    Yang, Wu-Lin
    Tang, Wenjun
    Deng, Wei-Ping
    ORGANIC LETTERS, 2018, 20 (01) : 104 - 107
12345