Styrylmalonates as an Alternative to Donor-Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones

被引：29
|
作者：
Borisov, Denis D. [1 ]
Novikov, Roman A. [1 ,2 ]
Eltysheva, Anna S. [1 ]
Tkachev, Yaroslav V. [2 ]
Tomiloy, Yury V. [1 ]
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia
[2] Russian Acad Sci, Engelhardt Inst Mol Biol, 32 Vavilov St, Moscow 119991, Russia
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 14期
基金：
俄罗斯科学基金会;
关键词：
AROMATIC-ALDEHYDES; DERIVATIVES; CYCLOADDITION; NITROSOARENES; CONSTRUCTION; ANNULATION; MECHANISM;
D O I：
10.1021/acs.orglett.7b01556
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new strategy for modifying the reactivity of donor-acceptor cyclopropanes (DAC) has been suggested. It involves the use of isomeric styrylmalonates as alternative sources of reactive intermediates. The efficiency of the approach has been demonstrated in reactions with aromatic aldehydes. As a result, a new process for Construction of the 5,6-dihydropyran-2-one skeleton has been developed. It efficiently occurs with high diastereoselectivity in the presence of BF3.Et(2)Q; the products can be easily isolated by crystallization. The subsequent use of the resulting dihydropyranones in syntheses providing convenient access to various classes of compounds with broad molecular diversity has been demonstrated.
引用
收藏
页码：3731 / 3734
页数：4
相关论文
共 50 条
  • [41] Ferrocenyl-substituted tetrahydrothiophenes via formal [3+2]-cycloaddition reactions of ferrocenyl thioketones with donor-acceptor cyclopropanes
    Mloston, Grzegorz
    Kowalczyk, Mateusz
    Augustin, Andre U.
    Jones, Peter G.
    Werz, Daniel B.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 1288 - 1295
  • [42] Stereoretentive Catalytic [3+2]-Cycloaddition/Rearrangement/Decarboxylation Reactions of Indoles with Non-Racemic Donor-Acceptor Cyclopropanes
    Bao, Ming
    Lopez, Karlos
    Gurung, Raj
    Arman, Hadi
    Doyle, Michael P.
    ACS CATALYSIS, 2023, 13 (03) : 1621 - 1629
  • [43] Synthesis of Perfluoroalkyl-Substituted γ-Lactones and 4,5-Dihydropyridazin-3(2H)-ones via Donor-Acceptor Cyclopropanes
    Gladow, Daniel
    Reissig, Hans-Ulrich
    HELVETICA CHIMICA ACTA, 2012, 95 (10) : 1818 - 1830
  • [44] DBU-Mediated [3+2] Cycloaddition Reactions of Donor-Acceptor Cyclopropanes with Nitromethane: Efficient Strategy for the Construction of Isoxazole Skeletons
    Xue, Shuwen
    Liu, Jiaming
    Wang, Cunde
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (14) : 2450 - 2456
  • [45] Solvent-Free DABCO-Mediated [3+2] Cycloadditions of Donor-Acceptor Cyclopropanes with Aldehydes: Strategy for Synthesis of Fully Substituted Furans
    Liu, Jiaming
    Ye, Weijian
    Qng, Xushun
    Wang, Cunde
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (17): : 7970 - 7976
  • [46] Construction of Isoxazolidines through Formal [3+2] Cycloaddition Reactions of in situ Generated Nitrosocarbonyls with Donor-Acceptor Cyclopropanes: Synthesis of -Amino -Butyrolactones
    Varshnaya, Rohit Kumar
    Banerjee, Prabal
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (23) : 4059 - 4066
  • [47] Diastereoselective [3+2] Cycloaddition of Quinoxalin-2(1H)-ones with Donor-Acceptor Cyclopropanes: Efficient Synthesis of Tetrahydro pyrrolo[1,2-a]quinoxalin-4(5H)-ones
    Dutta, Himangsu Sekhar
    Ahmad, Ashfaq
    Khan, Afsar Ali
    Kumar, Mohit
    Raziullah
    Vaishnav, Jayanti
    Gangwar, Manoj
    Ampapathi, Ravi Sankar
    Koley, Dipankar
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 16558 - 16572
  • [48] Synthesis and Photovoltaic Properties of a Donor-Acceptor Copolymer of Dithienosilole and 5,6-Bis(octyloxy)benzo[1,2,5]thiadiazole
    Huang, Youguang
    Zhang, Maojie
    Jing, Yan
    Fan, Huili
    Guo, Xia
    Li, Yongfang
    MACROMOLECULAR CHEMISTRY AND PHYSICS, 2012, 213 (23) : 2529 - 2535
  • [49] Donor-acceptor polymers based on 5,6-difluoro-benzo[1,2,5]thiadiazole for high performance solar cells
    Tang, Dandan
    Liu, Yanfeng
    Zhang, Zhe
    Shu, Qinghai
    Wang, Bin
    Fan, Jian
    Song, Bo
    ORGANIC ELECTRONICS, 2016, 33 : 187 - 193
  • [50] BF 3 <middle dot>OEt 2 -Mediated (3+2) Cycloaddition Reactions of Donor-Acceptor Cyclopropanes (DACs) with Cyanamides: Access to Cyclic Amidines
    Gopal, Braj
    Singh, Prasoon Raj
    Bhatt, Shubham
    Goswami, Avijit
    SYNTHESIS-STUTTGART, 2024, 56 (16): : 2521 - 2528
12345