Ring-Opening Regio-, Diastereo-, and Enantioselective 1,3 Chlorochalcoge nation of Cyclopropyl Carbaldehydes

被引：64
|
作者：
Wallbaum, Jan [1 ]
Garve, Lennart K. B. [1 ]
Jones, Peter G. [2 ]
Werz, Daniel B. [1 ]
机构：
[1] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, Hagenring 30, D-38106 Braunschweig, Germany
[2] Tech Univ Carolo Wilhelmina Braunschweig, Inst Inorgan & Analyt Chem, Hagenring 30, D-38106 Braunschweig, Germany
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 52期
基金：
欧洲研究理事会;
关键词：
1,3-bisfunctionalization; cyclopropane; enantioselectivity; organocatalysis; sulfur; DONOR-ACCEPTOR CYCLOPROPANES; DIELS-ALDER REACTION; CYCLOADDITION REACTIONS; ORGANIC CATALYSIS; ENAMINE CATALYSIS; ALPHA; BETA-UNSATURATED ALDEHYDES; 1,3-DIPOLAR CYCLOADDITION; SULFENYL CHLORIDES; ALPHA-ALKYLATION; PHENYL SELENIDE;
D O I：
10.1002/chem.201605265
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
meso-Cyclopropyl carbaldehydes are treated in the presence of an organocatalyst with sulfenyl and selenyl chlorides to afford 1,3chlorochal cogenated products. The transformation is achieved by a merged iminium-enamine activation. The enantioselective desymmetrization reaction, leading to three adjacent stereocenters, furnished the target products in complete regioselectivity and moderate to high diastereo- and enantioselectivities (d.r. up to 15:1 and e.r. up to 93:7).
引用
收藏
页码：18756 / 18759
页数：4
相关论文
共 50 条
  • [1] Cobalt-Catalyzed Regio-, Diastereo- and Enantioselective Reductive Coupling of 1,3-Dienes and Aldehydes
    Wang, Yu
    Wang, Danrui
    Wang, Shilin
    Chong, Qinglei
    Zhang, Zhihan
    Meng, Fanke
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (01)
  • [2] Substrate Directed Regio- and Enantioselective Ring-Opening of Epoxides and Aziridines
    Sun, Wen-Na
    Mei, Guang-Jian
    Jia, Shi-Kun
    CHEMCATCHEM, 2024, 16 (08)
  • [3] Highly regio-, diastereo- and enantioselective deracemization of axially chiral 3-alkylideneoxindoles
    Mei, Hongjiang
    Lin, Lili
    Wang, Lifeng
    Dai, Li
    Liu, Xiaohua
    Feng, Xiaoming
    CHEMICAL COMMUNICATIONS, 2017, 53 (62) : 8763 - 8766
  • [4] Cobalt-Catalyzed Regio-, Diastereo- and Enantioselective Intermolecular Hydrosilylation of 1,3-Dienes with Prochiral Silanes
    Wang, Lei
    Lu, Wenxin
    Zhang, Jiwu
    Chong, Qinglei
    Meng, Fanke
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (30)
  • [5] Metal-Catalyzed Directed Regio- and Enantioselective Ring-Opening of Epoxides
    Wang, Chuan
    Luo, Lan
    Yamamoto, Hisashi
    ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (02) : 193 - 204
  • [6] Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles
    Trost, Barry M.
    Zhang, Yong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (47) : 14548 - +
  • [7] Highly Regio-, Diastereo-, and Enantioselective Rhodium-Catalyzed Intramolecular Cyclopropanation of (Z)-1,3-Dienyl Aryldiazoacetates
    Marichev, Kostiantyn O.
    Ramey, Justin T.
    Arman, Hadi
    Doyle, Michael P.
    ORGANIC LETTERS, 2017, 19 (06) : 1306 - 1309
  • [8] Chemo-, Regio-, Diastereo-, and Enantioselective Palladium Allylic Alkylation of 1,3-Dioxaboroles as Synthetic Equivalents of α-Hydroxyketones
    Trost, Barry M.
    Schultz, Johnathan E.
    Chang, Taiwei
    Maduabum, Michael R.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (24) : 9521 - 9526
  • [9] Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles
    Trost, Barry M.
    Zhang, Yong
    Journal of the American Chemical Society, 2007, 129 (47): : 14548 - 14549
  • [10] Direct Regio-, Diastereo-, and Enantioselective Vinylogous Michael Addition of Prochiral 3-Alkylideneoxindoles to Nitroolefins
    Rassu, Gloria
    Zambrano, Vincenzo
    Pinna, Luigi
    Curti, Claudio
    Battistini, Lucia
    Sartori, Andrea
    Pelosi, Giorgio
    Zanardi, Franca
    Casiraghi, Giovanni
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (09) : 1881 - 1886
12345