Rh(II)-Catalyzed Cyclopropanation of Furans and Its Application to the Total Synthesis of Natural Product Derivatives

被引：42
|
作者：
Lehner, Verena [1 ,2 ]
Davies, Huw M. L. [2 ]
Reiser, Oliver [1 ]
机构：
[1] Univ Regensburg, Inst Organ Chem, Univ Str 31, D-93053 Regensburg, Germany
[2] Emory Univ, Dept Chem, 1515 Dickey Dr, Atlanta, GA 30322 USA
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 18期
基金：
美国国家科学基金会;
关键词：
ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; STABILIZED VINYLCARBENOIDS; CATALYZED DECOMPOSITION; RHODIUM CARBENOIDS; TURNOVER NUMBERS; RH(II) CATALYST; PYRROLES; DIRHODIUM(II); CONVERSION;
D O I：
10.1021/acs.orglett.7b02009
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Rh(II)-catalyzed enantioselective cyclopropanations of furans, providing access to synthetically useful building blocks, are reported. After screening of 10 Rh(II) catalysts, Rh-2(S-TCPTTL)(4) was identified as a highly efficient and selective catalyst (up to 98% ee, TON 88000, and TOF 24/s) for the cydopropanation of furans. These cyclopropanes were successfully applied to the enantioselective synthesis of novel paraconic acid derivatives.
引用
收藏
页码：4722 / 4725
页数：4
相关论文
共 50 条
  • [41] Enantioselective Allenation of Terminal Alkynes Catalyzed by Copper Halides of Mixed Oxidation States and Its Application to the Total Synthesis of Scorodonin
    Wu, Guolin
    Yao, Yuan
    Li, Gen
    Zhang, Xue
    Qian, Hui
    Ma, Shengming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (04)
  • [42] Rh(II)-catalyzed intramolecular annulation of N-sulfonyl 1,2,3-triazoles with indole derivatives: a new method for synthesis pyranoindoles
    Xie, Hui
    Yang, Jian-Xin
    Bora, Pranjal Protim
    Kang, Qiang
    TETRAHEDRON, 2016, 72 (22) : 3014 - 3021
  • [43] Palladium-catalyzed asymmetric synthesis of cyclohexene derivatives having the substituents at the 2-position and the application to the syntheses of the natural products
    Mori, M
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2002, 60 (01) : 15 - 25
  • [44] Asymmetric Total Synthesis and Evaluation of Antitumor Activity of Ophiorrhisine A and Its Derivatives
    Onozawa, Tadayoshi
    Kitajima, Mariko
    Kogure, Noriyuki
    Takayama, Hiromitsu
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (24) : 15312 - 15322
  • [45] Heterogeneous Copper-Catalyzed Cross-Coupling for Sustainable Synthesis of Chiral Allenes: Application to the Synthesis of Allenic Natural Products
    Wu, Haibo
    Zheng, Zhiyao
    Zhang, Kaiheng
    Kajanus, Johan
    Johansson, Magnus J.
    Cordova, Armando
    Baeckvall, Jan-E.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (50)
  • [46] A Flexible Asymmetric Approach to Methyl 5-Alkyltetramates and Its Application in the Synthesis of Cytotoxic Marine Natural Product Belamide A
    Lan, Hong-Qiao
    Ye, Jian-Liang
    Wang, Ai-E
    Ruan, Yuan-Ping
    Huang, Pei-Qiang
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (03) : 958 - 968
  • [47] Total Synthesis and Structural Revision of Mycalol, an Anticancer Natural Product from the Marine Source
    Seetharamsingh, B.
    Rajamohanan, P. R.
    Reddy, D. Srinivasa
    ORGANIC LETTERS, 2015, 17 (07) : 1652 - 1655
  • [48] Total synthesis of dendrobate alkaloid (+)-241D, isosolenopsin and isosolenopsin A: application of a gold-catalyzed cyclization
    Gouault, Nicolas
    Le Roch, Myriam
    de Campos Pinto, Gisele
    David, Michele
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (29) : 5541 - 5546
  • [49] Stereoselective Rh2(S-IBAZ)4-Catalyzed Cyclopropanation of Alkenes, Alkynes, and Allenes: Asymmetric Synthesis of Diacceptor Cyclopropylphosphonates and Alkylidenecyclopropanes
    Lindsay, Vincent N. G.
    Fiset, Dominic
    Gritsch, Philipp J.
    Azzi, Soula
    Charette, Andre B.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) : 1463 - 1470
  • [50] Synthesis of 1-aminoindole derivatives via Rh(iii)-catalyzed annulation reactions of hydrazines with sulfoxonium ylides
    Xie, Wucheng
    Chen, Xin
    Shi, Junjun
    Li, Jieshen
    Liu, Riyao
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (15) : 2662 - 2666
12345