Synthesis of pyrroloindolines through formal [3+2]-cycloaddition of indoles with chiral N-2-acetamidoacrylyl oxazolidinones

被引：2
|
作者：
Smith, Isaac T. [1 ]
Neeley, Jared B. [1 ]
Brinley, Tanner D. [1 ]
Fullmer, Peter R. [1 ]
Andrus, Merritt B. [1 ]
机构：
[1] Brigham Young Univ, Dept Chem & Biochem, C100 BNSN, Provo, UT 84602 USA
来源：
TETRAHEDRON LETTERS | 2020年 / 61卷 / 23期
关键词：
Pyrroloindoline; Oxazolidinone; 3,2]-Cycloaddition; Tin(IV) chloride; ENANTIOSELECTIVE SYNTHESIS; 3+2 CYCLOADDITION; CONCISE SYNTHESIS; CONSTRUCTION; CYCLIZATION; AMAUROMINE; STRATEGY; NOCARDIOAZINES; TRYPTAMINES; AUXILIARIES;
D O I：
10.1016/j.tetlet.2020.151947
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chiral N-2-acetamidoacrylyl oxazolidinones were produced and reacted with indoles under Lewis acid conditions to generate hexahydropyrrolo[2,3-b]indole products in a formal [3 + 2] cycloaddition process. Optimal conditions included the use of tin(IV) chloride in methylene chloride at 0 degrees C. Pyrroloindoline products were obtained from various indoles with shorter reaction times (12 hr) up to 91% yield with high, >20:1 exo selectivity. A mechanism involving reversible conjugate addition followed by an enamine lone-pair-iminium capture, tautomerization, and tin-enolate protonation accounts for the selectivity. The method enables selective applications to pyrroloindoline targets and further refinement with chiral catalysts. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数：5
相关论文
共 50 条
  • [31] Photoactivated Formal [3+2]/[4+2] Cycloaddition of N-Aryl Cyclopropyl and Cyclobutylamines
    Villela, Lucas F.
    Zidan, Montserrat
    Barriault, Louis
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (44)
  • [32] Scope of the formal [3+2] cycloaddition for the synthesis of substituted 3-arylindanes and related compounds
    Lantano, Beatriz
    Aguirre, Jose Manuel
    Ugliarolo, Esteban Ariel
    Benegas, Maria Laura
    Moltrasio, Graciela Yolanda
    TETRAHEDRON, 2008, 64 (18) : 4090 - 4102
  • [33] Studies on the Formal [3+2] Cycloaddition of Aziridines with Alkenes for the Synthesis of 1-Azaspiroalkanes
    Martinand-Lurin, Elodie
    Gruber, Raymond
    Retailleau, Pascal
    Fleurat-Lessard, Paul
    Dauban, Philippe
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03): : 1414 - 1426
  • [34] Synthesis of Ferrocenyl Pyrrolizidines Through [3+2] Cycloaddition of Azomethine Ylides
    Zhang, Yu-Mei
    Liu, Peng
    Zhang, Hong-Li
    SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2013, 43 (03) : 340 - 342
  • [35] SYNTHESIS OF DIHYDRO-1H-INDENES VIA A FORMAL 3+2 CYCLOADDITION
    ANGLE, SR
    ARNAIZ, DO
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 200 : 112 - ORGN
  • [36] Formal [3+2] cycloaddition of Ugi adducts towards pyrrolines
    Ben Abdessalem, Abdelbari
    Abderrahim, Raoudha
    Agrebie, Asma
    Dos Santos, Aurelie
    El Kaim, Laurent
    Komesky, Andrew
    CHEMICAL COMMUNICATIONS, 2015, 51 (06) : 1116 - 1119
  • [37] Methylenecyclopentane annulation via formal [3+2] cycloaddition reaction
    Takahashi, Y
    Tanino, K
    Kuwajima, I
    TETRAHEDRON LETTERS, 1996, 37 (33) : 5943 - 5946
  • [38] Diastereoselective Synthesis of Chiral 2,3-Disubstituted lndolines via Formal [3+2]-Cycloaddition of Arynes with γ-Amino-α,β-unsaturated Esters
    Aher, Ravindra D.
    Suryavanshi, Gurunath M.
    Sudalai, Arumugam
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (11): : 5940 - 5946
  • [39] Formal [3+2] Cycloaddition of Ketenes and Oxaziridines Catalyzed by Chiral Lewis Bases: Enantioselective Synthesis of Oxazolin-4-ones
    Shao, Pan-Lin
    Chen, Xiang-Yu
    Ye, Song
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (45) : 8412 - 8416
  • [40] Formal [3+2] dipolar cycloaddition reactions of nitrocyclopropane carboxylates
    Hardman, Andrea M.
    So, Sonia S.
    Mattson, Anita E.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
12345