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

被引：65
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 68 条
  • [1] Silylmethyl-substituted cyclopropyl and other strained ring systems: cycloaddition with dipolarophiles
    Agrawal, Divya
    Yadav, Veejendra K.
    [J]. CHEMICAL COMMUNICATIONS, 2008, (48) : 6471 - 6488
  • [2] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction
    Ahrendt, KA
    Borths, CJ
    MacMillan, DWC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) : 4243 - 4244
  • [3] [Anonymous], 2015, Acta Crystallogr., V71, P3
  • [4] [Anonymous], 2004, ANGEW CHEM
  • [5] [Anonymous], 2015, Angew. Chem.
  • [6] [Anonymous], 2008, ANGEW CHEM
  • [7] [Anonymous], 2013, CRYSALISPRO
  • [8] Organocatalytic Enantioselective Olefin Aminofluorination
    Appayee, Chandrakumar
    Brenner-Moyer, Stacey E.
    [J]. ORGANIC LETTERS, 2010, 12 (15) : 3356 - 3359
  • [9] Total Synthesis of (-)-Spinosyn A via Carbonylative Macrolactonization
    Bai, Yu
    Shen, Xingyu
    Li, Yong
    Dai, Mingji
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (34) : 10838 - 10841
  • [10] Organocatalytic enantioselective desymmetrisation
    Borissov, A.
    Davies, T. Q.
    Ellis, S. R.
    Fleming, T. A.
    Richardson, M. S. W.
    Dixon, D. J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (20) : 5474 - 5540
1234567