Enantioselective Ammonium Ylide Mediated One-Pot Synthesis of Highly Substitutedγ-Butyrolactones

被引：13
|
作者：
Drennhaus, Till [2 ]
Oehler, Laura [1 ]
Djalali, Saveh [1 ]
Hoefmann, Svenja [1 ]
Mueller, Clemens [1 ]
Pietruszka, Joerg [1 ,2 ]
Worgull, Dennis [1 ]
机构：
[1] Heinrich Heine Univ Dusseldorf, Forschungszentrum Julich, Inst Bioorgan Chem, Stetternicher Forst, Bldg 15-8, D-52426 Julich, Germany
[2] Forschungszentrum Julich, Inst Bio & Geosci IBG 1, D-52426 Julich, Germany
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 12期
关键词：
asymmetric synthesis; asymmetric catalysis; heterocycles; lactones; multicomponent reactions; ylides; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; CINCHONA ALKALOIDS; DIASTEREOSELECTIVE SYNTHESIS; FACILE SYNTHESIS; 4+1 ANNULATION; EFFICIENT; DERIVATIVES; CYCLOPROPANATION; QUATERNARY;
D O I：
10.1002/adsc.202000039
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An ammonium ylide mediated access towardstrans-beta,gamma-disubstituted,all-trans-alpha,beta,gamma-trisubstituted, and alpha,alpha,beta,gamma-tetrasubstituted gamma-butyrolactones bearing a broad variety of functionalities was developed. Starting from widely accessible benzylidene Meldrum's acid derivatives and alpha-bromo carbonyl compounds,gamma-butyrolactones were obtained in yields between 32-99% with up to excellent diastereoselectivities (>95:5)viaa DABCO-mediated [2+1] annulation. Utilization of enantiomerically pure cinchona alkaloid derivatives enables the first asymmetric ammonium ylide mediated method to provide (3R, 4R)-beta,gamma-disubstituted and (2R, 3R, 4R)-alpha,beta,gamma-trisubstituted gamma-butyrolactones in moderate to good yields with up to very good enantiomeric ratios (97:3). The scalability of the transformation was proven while determining the absolute configuration.
引用
收藏
页码：2385 / 2396
页数：12
相关论文
共 50 条
  • [41] One-pot synthesis of highly substituted imidazoles using molecular iodine: A versatile catalyst
    Kidwai, Mazaahir
    Mothsra, Poonam
    Bansal, Vikas
    Somvanshi, Rishi K.
    Ethayathulla, Abdul S.
    Dey, Sharmistha
    Singh, Tej P.
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 265 (1-2) : 177 - 182
  • [42] An efficient one-pot synthesis of highly substituted furans catalyzed by N-bromosuccinimide
    Ghasemnejad-Bosra, Hassan
    Faraje, Mohammad
    Habibzadeh, Setareh
    Ramzanian-Lehmali, Farhad
    JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2010, 75 (03) : 299 - 305
  • [43] One-Pot Highly Diastereoselective Synthesis of cis-Vinylaziridines via the Sulfur Ylide-Mediated Aziridination and Palladium(0)-Catalyzed Isomerization
    Zhu, Ben-Hu
    Zheng, Jun-Cheng
    Yu, Chang-Bin
    Sun, Xiu-Li
    Zhou, Yong-Gui
    Shen, Qi
    Tang, Yong
    ORGANIC LETTERS, 2010, 12 (03) : 504 - 507
  • [44] Isothiourea-Mediated One-Pot Synthesis of Trifluoromethyl Substituted 2-Pyrones
    Yeh, Pei-Pei
    Daniels, David S. B.
    Cordes, David B.
    Slawin, Alexandra M. Z.
    Smith, Andrew D.
    ORGANIC LETTERS, 2014, 16 (03) : 964 - 967
  • [45] Solvent-mediated One-pot Synthesis of Cyclic N-Substituted Imides
    Patil, Sambhaji V.
    Mahale, Keshao A.
    Gosavi, Kirankumar S.
    Deshmukh, Ganesh B.
    Patil, Nilesh S.
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2013, 45 (04) : 314 - 320
  • [46] Direct one-pot highly enantioselective assembly of polyketide and carbohydrate synthons
    Zhao, Gul-Ling
    Liao, Wei-Wei
    Cordova, Armando
    TETRAHEDRON LETTERS, 2006, 47 (28) : 4929 - 4932
  • [47] First ultrasound-mediated one-pot synthesis of N-substituted amides
    Srivastava, Rajendra M.
    Neves Filho, Ricardo A. W.
    da Silva, Cecilia A.
    Bortoluzzi, Adailton J.
    ULTRASONICS SONOCHEMISTRY, 2009, 16 (06) : 737 - 742
  • [48] HMPT ZINC MEDIATED ONE-POT CONVENIENT SYNTHESIS OF BETA-SUBSTITUTED ACRYLATES
    KHAN, RH
    RASTOGI, RC
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1992, 31 (04): : 276 - 276
  • [49] One-Pot Catalytic Enantioselective Synthesis of 2-Pyrazolines
    Thomson, Connor J.
    Barber, David M.
    Dixon, Darren J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (08) : 2469 - 2473
  • [50] Enantioselective one-pot three-component synthesis of propargylamines
    Bisai, Alakesh
    Singh, Vinod K.
    ORGANIC LETTERS, 2006, 8 (11) : 2405 - 2408
12345