A highly efficient enantioselective synthesis of 2-methyl chromans via four sequential palladium-catalyzed reactions

被引:14
|
作者
Palucki, M [1 ]
Yasuda, N [1 ]
机构
[1] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
关键词
palladium; chroman; asymmetric;
D O I
10.1016/j.tetlet.2004.12.043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective synthesis of substituted 2-methyl chromans was accomplished in four steps using four sequential Pd-catalyzed reactions. A study of the key palladium-catalyzed regioselective aryl ether ring fort-nation of two different substrates was also carried out to better understand the factors which affect the selectivity of the reaction. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:987 / 990
页数:4
相关论文
共 50 条
  • [21] Highly Efficient Synthesis of Cephalotaxine by Two Palladium-Catalyzed Cyclizations
    Institut für Organische Chemie, Universität, Tammannstrasse 2, D-37077 Göttingen, Germany
    Angew Chem (Int Ed Engl), 10 (1124-1125):
  • [22] Highly Efficient Four-Component Synthesis of 4(3H)-Quinazolinones: Palladium-Catalyzed Carbonylative Coupling Reactions
    He, Lin
    Li, Haoquan
    Neumann, Helfried
    Beller, Matthias
    Wu, Xiao-Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (05) : 1420 - 1424
  • [23] Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions
    Ibrahim, Mansur B.
    El Ali, Bassam
    Malik, Imran
    Fettouhi, Mohammed
    TETRAHEDRON LETTERS, 2016, 57 (05) : 554 - 558
  • [24] Synthesis of thiophene derivatives via palladium-catalyzed coupling reactions
    Arai, Nobumichi
    Miyaoku, Takayuki
    Teruya, Shota
    Mori, Atsunori
    TETRAHEDRON LETTERS, 2008, 49 (06) : 1000 - 1003
  • [25] STEREOCONTROLLED SYNTHESIS OF TROPANOL DERIVATIVES VIA PALLADIUM-CATALYZED REACTIONS
    BACKVALL, JE
    RENKO, ZD
    BYSTROM, SE
    TETRAHEDRON LETTERS, 1987, 28 (36) : 4199 - 4202
  • [26] Synthesis of natural products via stereocontrolled palladium-catalyzed reactions
    Bäckvall, JE
    PURE AND APPLIED CHEMISTRY, 1999, 71 (06) : 1065 - 1070
  • [27] Synthesis of Tricyclic Isoxazoles via Sequential [3+2] Dipolar Cycloaddition and Palladium-Catalyzed Intramolecular Arylation Reactions
    Guo, Dong-Cai
    Zhang, Chao
    Li, Fei
    Zhang, Fenghua
    Yu, Fang
    He, Yu-Peng
    SYNTHESIS-STUTTGART, 2017, 49 (06): : 1356 - 1370
  • [28] An efficient enantioselective synthesis of strigolactones with a palladium-catalyzed asymmetric coupling as the key step
    Reizelman, A
    Zwanenburg, B
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (05) : 810 - 814
  • [29] Palladium-Catalyzed Sequential Reactions via Allene Intermediates for the Rapid Synthesis of Fused Polycyclic Pyrrole Derivatives
    Huang, Xian
    Zhu, Shugao
    Shen, Ruwei
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) : 3118 - 3122
  • [30] Efficient Synthesis of (-)-Corynoline by Enantioselective Palladium-Catalyzed α-Arylation with Sterically Hindered Substrates
    Rao, Xiaofeng
    Li, Naikai
    Bai, Heng
    Dai, Chaodi
    Wang, Zheng
    Tang, Wenjun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (38) : 12328 - 12332