Synthesis of Chiral 2,3-Dihydrofurans via One-Pot Pd-Catalyzed Asymmetric Allylic Cycloaddition and a Retro-Dieckmann Fragmentation Cascade

被引：3
|
作者：
Shah, Babar Hussain [1 ,2 ]
Khan, Sardaraz [1 ,2 ]
Zhao, Can [1 ,2 ]
Zhang, Yong Jian [1 ,2 ,3 ]
机构：
[1] Tong Univ, Frontiers Sci Ctr Transformat Mol, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China
[2] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
[3] Shanghai Jiao Tong Univ, Sichuan Res Inst, Chengdu 610042, Sichuan, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 16期
基金：
中国国家自然科学基金;
关键词：
FORMAL 3+2 CYCLOADDITION; VINYLETHYLENE CARBONATES; DECARBOXYLATIVE CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; BETA-KETOESTERS; DIHYDROFURANS; CONSTRUCTION; ALLYLATION; DITERPENES; ACCESS;
D O I：
10.1021/acs.joc.3c00976
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the enantioselective synthesisof 2,3-dihydrofuransbearing a quaternary stereocenter has been developed via Pd-catalyzedasymmetric allylic cycloaddition and a retro-Dieckmann Fragmentationcascade. The asymmetric allylic cycloaddition of vinylethylene carbonateswith 3-cyanochromone followed by base-assisted retro-Dieckmann fragmentationproceeded smoothly via a one-pot process to produce chiral 3,4-disubstituted2,3-dihydrofurans in high yields with excellent enantioselectivities.
引用
收藏
页码：12100 / 12104
页数：5
相关论文
共 50 条
  • [1] Pd-Catalyzed Asymmetric Allylic Substitution Cascade of But-2-ene-1,4-diyl Dimethyl Dicarbonate for the Synthesis of Chiral 2,3-Dihydrofurans
    Liu, Hao
    Sun, Zhenliang
    Xu, Kai
    Zheng, Yan
    Liu, Delong
    Zhang, Wanbin
    [J]. ORGANIC LETTERS, 2020, 22 (12) : 4680 - 4685
  • [2] A Pd-catalyzed asymmetric allylic substitution cascade via an asymmetric desymmetrization for the synthesis of bicyclic dihydrofurans
    Xu, Kai
    Liu, Hao
    Hou, Yilin
    Shen, Jiefeng
    Liu, Delong
    Zhang, Wanbin
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (88) : 13295 - 13298
  • [3] Direct Access to Highly Enantioenriched α-Branched Acrylonitriles through a One-Pot Sequential Asymmetric Michael Addition/Retro-Dieckmann/Retro-Michael Fragmentation Cascade
    Duchemin, Nicolas
    Cattoen, Martin
    Gayraud, Oscar
    Anselmi, Silvia
    Siddiq, Bilal
    Buccafusca, Roberto
    Daumas, Marc
    Ferey, Vincent
    Smietana, Michael
    Arseniyadis, Stellios
    [J]. ORGANIC LETTERS, 2020, 22 (15) : 5995 - 6000
  • [4] N-Phenacylpyridinium bromides in the one-pot synthesis of 2,3-dihydrofurans
    Chuang, Che-Ping
    Chen, Kuang-Po
    [J]. TETRAHEDRON, 2012, 68 (05) : 1401 - 1406
  • [5] Asymmetric Synthesis of 2,3-Dihydrofurans by One-Pot Michael Addition/I2-Mediated Cyclization
    Zhang, Xiao-Long
    Feng, Kai-Xiang
    Xia, Ai-Bao
    Zheng, Ya-Yun
    Li, Chen
    Du, Xiao-Hua
    Xu, Dan-Qian
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (23) : 2918 - 2925
  • [6] Asymmetric Synthesis of 2,3-Dihydrofurans via Squaramide Catalyzed Michael-Alkylation Reaction
    Ma, Zhi-Wei
    Wang, Chuan-Chuan
    Chen, Xiao-Pei
    Sun, Bin
    Tao, Jing-Chao
    Lv, Quan-Jian
    [J]. LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (10) : 913 - 917
  • [7] "One-pot" synthesis of amidoxime via Pd-catalyzed cyanation and amidoximation
    Yang, Chu-Ting
    Han, Jun
    Liu, Jun
    Gu, Mei
    Li, Yi
    Wen, Jun
    Yu, Hai-Zhu
    Hu, Sheng
    Wang, Xiaolin
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (09) : 2541 - 2545
  • [8] Synthesis of Chiral α,β-Unsaturated γ-Amino Esters via Pd-Catalyzed Asymmetric Allylic Amination
    Xia, Chao
    Shen, Jiefeng
    Liu, Delong
    Zhang, Wanbin
    [J]. ORGANIC LETTERS, 2017, 19 (16) : 4251 - 4254
  • [9] Enantioselective synthesis of chiral phosphonylated 2,3-dihydrofurans by copper catalyzed asymmetric formal [3+2] cycloaddition of propargylic esters with β-keto phosphonates
    Chen, Xiushuai
    Hou, Chuanjin
    Li, Qing
    Liu, Yanjun
    Yang, Ruifeng
    Hu, Xiangping
    [J]. CHINESE JOURNAL OF CATALYSIS, 2016, 37 (08) : 1389 - 1395
  • [10] Chiral carbon-sulfur center formation via Pd-catalyzed asymmetric allylic thioetherification: synthesis of allylic thioethers
    Cai, Junmei
    Cai, Juewang
    Zheng, Purui
    Wang, Xiaorong
    Zhao, Xiaoming
    [J]. RSC ADVANCES, 2017, 7 (01): : 256 - 259
12345