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
  • [21] A CONVENIENT ONE-POT THREE COMPONENT APPROACH TO SYNTHESIS OF HIGHLY SUBSTITUTED IMINOTHIAZOLINES
    Samimi, Heshmat Allah
    Mamaghani, Manouchehr
    Tabatabaeian, Khalil
    HETEROCYCLES, 2008, 75 (11) : 2825 - +
  • [22] Synthesis of Highly Substituted Cyclobutanones by a One-Pot Keteniminium-Enamine Process
    Dagoneau, Dylan
    Kolleth, Amandine
    Quinodoz, Pierre
    Horoz, Beyza
    Catak, Saron
    Lumbroso, Alexandre
    Sulzer-Mosse, Sarah
    De Mesmaeker, Alain
    HELVETICA CHIMICA ACTA, 2021, 104 (05)
  • [23] Facile one-pot synthesis of highly substituted heterocycles from allenes.
    Lotesta, SD
    Katukojvala, S
    Williams, LJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U140 - U140
  • [24] A simple one-pot, three-component, catalytic, highly enantioselective isoxazolidine synthesis
    Rios, Ramon
    Ibrahem, Ismail
    Vesely, Jan
    Zhao, Gui-Ling
    Cordova, Armando
    TETRAHEDRON LETTERS, 2007, 48 (32) : 5701 - 5705
  • [25] Indium trichloride catalyzed efficient one-pot synthesis of highly substituted furans
    Dey, Sumit
    Nandi, Debkumar
    Pradhan, Prasun K.
    Giri, Venkatachalam Sesha
    Jaisankar, Parasuraman
    TETRAHEDRON LETTERS, 2007, 48 (14) : 2573 - 2575
  • [26] A Highly Enantioselective One-Pot Synthesis of Spirolactones by an Organocatalyzed Michael Addition/Cyclization Sequence
    Sternativo, Silvia
    Calandriello, Antonella
    Costantino, Ferdinando
    Testaferri, Lorenzo
    Tiecco, Marcello
    Marini, Francesca
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) : 9382 - 9385
  • [27] Titanocene(III) chloride mediated radical-induced one-pot synthesis of α-methylene-γ-butyrolactones
    Paira, Moumita
    Banerjee, Biplab
    Jana, Samaresh
    Mandal, Samir Kumar
    Roy, Subhas Chandra
    TETRAHEDRON LETTERS, 2007, 48 (18) : 3205 - 3207
  • [28] One-pot synthesis of coumarin substituted dihydrofurans
    Chunduru, Venkata Sreenivasa Rao
    Vedula, Rajeswar Rao
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2012, 51 (09): : 1417 - 1420
  • [29] Efficient one-pot synthesis of substituted pyrazoles
    Tang, Meng
    Zhang, Fu-Min
    TETRAHEDRON, 2013, 69 (05) : 1427 - 1433
  • [30] A Novel One-Pot Synthesis of Substituted Quinolines
    Sabbagham, Maryam
    Yavari, Issa
    Hossaini, Zinatossadat
    Souri, Sannaz
    HELVETICA CHIMICA ACTA, 2010, 93 (05) : 946 - 950
12345