A Catalytic Asymmetric Synthesis of Polysubstituted Piperidines Using a Rhodium(I)-Catalyzed [2+2+2] Cycloaddition Employing a Cleavable Tether

被引：25
|
作者：
Martin, Timothy J. [1 ]
Rovis, Tomislav [1 ]
机构：
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 20期
关键词：
asymmetric synthesis; cycloaddition; heterocycles; ALKENYL ISOCYANATES; 2,6-DISUBSTITUTED PIPERIDINES; STEREOSELECTIVE-SYNTHESIS; ALKYNES; INDOLIZIDINES; CYCLIZATION; ALKALOIDS; FROG;
D O I：
10.1002/anie.201301741
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Break the cycle: The title reaction proceeds with a variety of alkyne substrates in good yield and high enantioselectivity. Upon reduction of the vinylogous amide in high diastereoselectivity (>19:1) and cleavage of the tether, N-methylpiperidine products with functional group handles can be accessed (see scheme). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：5368 / 5371
页数：4
相关论文
共 50 条
  • [11] Chemo- and Regioselective Rhodium(I)-Catalyzed [2+2+2] Cycloaddition of Allenynes with Alkynes
    Yasuda, Shigeo
    Kawaguchi, Yasuaki
    Okamoto, Yuta
    Mukai, Chisato
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (34) : 12181 - 12188
  • [12] RHODIUM-CATALYZED [2+2+2] CYCLOADDITION FOR THE SYNTHESIS OF SUBSTITUTED PYRIDINES, PYRIDONES, AND THIOPYRANIMINES
    Tanaka, Ken
    HETEROCYCLES, 2012, 85 (05) : 1017 - 1043
  • [13] Rhodium(I)-Catalyzed Intermolecular [2+2+2] Cycloaddition of Allenyl Aldehydes with Alkynes and Related Cyclization
    Oonishi, Yoshihiro
    Saito, Akira
    Sato, Yoshihiro
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (01) : 81 - 86
  • [14] Cationic rhodium(I)/modified-BINAP catalyzed [2+2+2] cycloaddition of alkynes with nitriles
    Tanaka, Ken
    Suzuki, Nanami
    Nishida, Goushi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (17) : 3917 - 3922
  • [15] Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition Reactions of 1,6-Enynes and Oxabenzonorbornadienes
    Ni, Jianxiao
    Chen, Jingchao
    Zhou, Yongyun
    Wang, Gaowei
    Li, Sida
    He, Zhenxiu
    Sun, Weiqing
    Fan, Baomin
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (15) : 3543 - 3547
  • [16] Rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and alkynes
    Yu, RT
    Rovis, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (09) : 2782 - 2783
  • [17] Asymmetric Synthesis of Axially Chiral Biaryl Diphosphine Ligands by Rhodium-Catalyzed Enantioselective Intramolecular Double [2+2+2] Cycloaddition
    Mori, Fumiya
    Fukawa, Naohiro
    Noguchi, Keiichi
    Tanaka, Ken
    ORGANIC LETTERS, 2011, 13 (03) : 362 - 365
  • [18] A rhodium(I)-xylyl-BINAP catalyzed asymmetric ynamide-[2+2+2] cycloaddition in the synthesis of optically enriched N,O-biaryls
    Oppenheimer, Jossian
    Johnson, Whitney L.
    Figueroa, Ruth
    Hayashi, Ryuji
    Hsung, Richard P.
    TETRAHEDRON, 2009, 65 (26) : 5001 - 5012
  • [19] Solid-phase synthesis of isoindolines via a rhodium-catalyzed [2+2+2] cycloaddition
    Sun, Q
    Zhou, XM
    Islam, K
    Kyle, DJ
    TETRAHEDRON LETTERS, 2001, 42 (37) : 6495 - 6497
  • [20] Facile Synthesis of Dibenzotetracenedione Derivatives by Rhodium-Catalyzed [2+2+2] Cycloaddition/Spontaneous Aromatization
    Aida, Yukimasa
    Shibata, Yu
    Tanaka, Ken
    CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (10) : 1823 - 1829
12345