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
  • [41] Regio- and Enantioselective Epoxy Ring Opening of 2,3-Epoxy-3-phenyl Alcohols/Carboxylic Acids and Their Derivatives
    Zhan, Xiaoyan
    Du, Xi
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (04) : 679 - 692
  • [42] Nickel-Catalyzed Regio- and Enantioselective Ring Opening of 3,4-Epoxy Amides and Esters with Aromatic Amines
    Liu, Jiawei
    Tang, Wei
    Wang, Chuan
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (31)
  • [43] SUBSTITUENT EFFECTS IN REGIO- AND STEREOSELECTIVE RING-OPENING REACTION OF AZIRIDINES WITH Et3N.3HF FOR β-FLUOROAMINE SYNTHESIS
    Sasaki, Shigeru
    Watanabe, Satono
    Shiino, Kaori
    Yanaka, Yuko
    Kaneko, Shiho
    Miyamoto, Kana
    Yasui, Ayano
    Sakaino, Hina
    Teramoto, Hiroyoshi
    Yamauchi, Takayasu
    Higashiyama, Kimio
    HETEROCYCLES, 2018, 97 (02) : 823 - 841
  • [44] Ring-opening of epoxyalcohols by diethylaluminium cyanide. Regio- and stereoselective synthesis of 1-cyano-2,3-diols
    Benedetti, F
    Berti, F
    Norbedo, S
    TETRAHEDRON LETTERS, 1999, 40 (05) : 1041 - 1044
  • [45] Corrigendum to: Cobalt-Catalyzed Regio-, Diastereo- and Enantioselective Intermolecular Hydrosilylation of 1,3-Dienes with Prochiral Silanes (Angewandte Chemie International Edition, (2022), 61, 30, 10.1002/anie.202205624)
    Wang, Lei
    Lu, Wenxin
    Zhang, Jiwu
    Chong, Qinglei
    Meng, Fanke
    Angewandte Chemie - International Edition, 2022, 61 (43):
  • [46] Regio- and Stereoselective Construction of Highly Functionalized 3-Benzazepine Skeletons through Ring-Opening Cycloamination Reactions Catalyzed by Gold
    Du, Xiangwei
    Yang, Shuang
    Yang, Jingyu
    Liu, Yuanhong
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (18) : 4981 - 4985
  • [47] Regio- and stereoselective ring opening of epoxides.: Enantioselective synthesis of 2,3,4-trisubstituted five-membered heterocycles
    Díez, D
    Beneitez, MT
    Marcos, IS
    Garrido, NM
    Basabe, P
    Urones, JG
    TETRAHEDRON-ASYMMETRY, 2002, 13 (06) : 639 - 646
  • [48] Ring-opening 1,3-arylboration of arylcyclopropanes mediated by BCl3
    Kuboki, Yuichi
    Arisawa, Mitsuhiro
    Murai, Kenichi
    RSC ADVANCES, 2020, 10 (62) : 37797 - 37799
  • [49] Regio- as well as stereoselective epoxide ring opening reactions using 3,3,3-trifluoroprop-1-yne
    Yamazaki, Takashi
    Iida, Minato
    Kawasaki-Takasuka, Tomoko
    Agou, Tomohiro
    JOURNAL OF FLUORINE CHEMISTRY, 2022, 257
  • [50] Cationic 3H-indolium dyes by ring-opening of benzo[1,3]oxazine
    Prostota, Yaroslav
    Coelho, Paulo J.
    DYES AND PIGMENTS, 2013, 98 (01) : 93 - 99
12345