Asymmetric Organocatalytic Michael Addition-Cyclization Cascade of Cyclopentane-1,2-dione with Substituted α,β-Unsaturated Aldehydes

被引：4
|
作者：
Preegel, Gert [1 ]
Silm, Estelle [1 ]
Kaabel, Sandra [1 ,2 ]
Jarving, Ivar [1 ]
Rissanen, Kari [2 ]
Lopp, Margus [1 ]
机构：
[1] Tallinn Univ Technol, Dept Chem & Biotechnol, Akad Tee 15, EE-12618 Tallinn, Estonia
[2] Univ Jyvaskyla, Dept Chem, Nanosci Ctr, POB 35, Jyvaskyla 40014, Finland
来源：
SYNTHESIS-STUTTGART | 2017年 / 49卷 / 14期
基金：
芬兰科学院;
关键词：
organocatalysis; asymmetry; diketones; dihydropyran; Michael addition; ENANTIOSELECTIVE SYNTHESIS; ENOL ETHER; CYCLOPENTANONE; TRANSFORMATION; CATALYSTS; ACCESS;
D O I：
10.1055/s-0036-1588787
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An asymmetric organocatalytic Michael addition-cyclization cascade reaction has been developed using cyclopentane-1,2-dione as a Michael donor and alpha, beta-unsaturated aldehydes as Michael acceptors. Bicyclic hemiacetals were obtained in excellent yields and enantioselectivities. On the basis of the results, a one-pot reaction has been developed to obtain chiral 3-substituted cyclopentane-1,2-diones and substituted dihydropyrans in good yields and excellent enantioselectivity.
引用
收藏
页码：3118 / 3125
页数：8
相关论文
共 29 条
  • [1] Enantioselective Organocatalytic Michael Addition-Cyclization Cascade of Cyclopentane-1,2-dione with Substituted (E)-2-oxobut-3-enoates
    Preegel, Gert
    Ilmarinen, Kaja
    Jaerving, Ivar
    Kanger, Tonis
    Pehk, Tonis
    Lopp, Margus
    SYNTHESIS-STUTTGART, 2015, 47 (23): : 3805 - 3812
  • [2] Asymmetric organocatalytic Michael addition of cyclopentane-1,2-dione to alkylidene oxindole
    Silm, Estelle
    Jarving, Ivar
    Kanger, Tonis
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2022, 18 : 167 - 173
  • [3] Asymmetric Organocatalytic Michael Addition-Cyclisation Cascade of Cyclopentane-1,2-dione with Alkylidene Malononitriles
    Silm, Estelle
    Kaabel, Sandra
    Jarving, Ivar
    Kanger, Tonis
    SYNTHESIS-STUTTGART, 2019, 51 (22): : 4198 - 4204
  • [4] Cyclopentane-1,2-dione bis(tert-butyldimethylsilyl) enol ether in asymmetric organocatalytic Mukaiyama-Michael reactions
    Reile, Indrek
    Paju, Anne
    Kanger, Tonis
    Jaerving, Ivar
    Lopp, Margus
    TETRAHEDRON LETTERS, 2012, 53 (12) : 1476 - 1478
  • [5] Asymmetric Organocatalytic Michael Addition-Cyclization Cascade Reaction of Nitroalkanes with o-Hydroxycinnamaldehydes
    Choi, Kwang-Su
    Kim, Sung-Gon
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (06) : 1119 - 1122
  • [6] Enantioselective organocatalytic Michael addition of cyclopentane-1,2-diones to electrophiles
    Preegel, Gert
    Noole, Artur
    Ilmarinen, Kaja
    Jaerving, Ivar
    Kanger, Tonis
    Pehk, Tonis
    Lopp, Margus
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [7] Enantioselective Organocatalytic Michael Addition of Cyclopentane-1,2-diones to Nitroolefins
    Preegel, Gert
    Noole, Artur
    Ilmarinen, Kaja
    Jaerving, Ivar
    Kanger, Tonis
    Pehk, Tonis
    Lopp, Margus
    SYNTHESIS-STUTTGART, 2014, 46 (19): : 2595 - 2600
  • [8] Asymmetric conjugate addition-cyclization of cyclohexane-1,2-dione with alkylidenemalononitriles using diaminomethylenemalononitrile organocatalyst
    Matsushima, Yasuyuki
    Iino, Yuta
    Tsuruta, Yuka
    Nakashima, Kosuke
    Hirashima, Shin-ichi
    Miura, Tsuyoshi
    TETRAHEDRON LETTERS, 2022, 97
  • [9] Asymmetric Organocatalytic Cascade Reactions with α-Substituted α,β-Unsaturated Aldehydes
    Galzerano, Patrizia
    Pesciaioli, Fabio
    Mazzanti, Andrea
    Bartoli, Giuseppe
    Melchiorre, Paolo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (42) : 7892 - 7894
  • [10] Asymmetric organocatalytic oxy-Michael addition of alcohols to α,β-unsaturated aldehydes
    Kano, Taichi
    Tanaka, Youhei
    Maruoka, Keiji
    TETRAHEDRON, 2007, 63 (35) : 8658 - 8664
123