Enamide-Benzyne-[2+2] Cycloaddition: Stereoselective Tandem [2+2]-Pericyclic Ring-Opening-Intramolecular N-Tethered [4+2] Cycloadditions

被引：92
|
作者：
Feltenberger, John B.
Hayashi, Ryuji
Tang, Yu
Babiash, Eric S. C.
Hsung, Richard P. [1 ]
机构：
[1] Univ Wisconsin, Dept Chem, Madison, WI 53705 USA
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 16期
关键词：
DIELS-ALDER REACTIONS; ELECTROCYCLIC REACTIONS; INWARD TORQUOSELECTIVITY; CATALYZED SYNTHESIS; MEDIATED SYNTHESIS; CHIRAL ENAMIDES; BENZYNE; ARYNES; SUBSTITUENT; HALIDES;
D O I：
10.1021/ol901434g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Benzyne-[2 + 2] cycloadditions with enamides are described. This effort led to the development of a highly stereoselective tandem [2 + 2] cycloaddition-pericyclic ring-opening-Intramolecular-N-tethered-[4 + 2] cycloaddition for rapid assembly of nitrogen heterocycles.
引用
收藏
页码：3666 / 3669
页数：4
相关论文
共 50 条
  • [1] Total Syntheses of Chelidonine and Norchelidonine via an Enamide-Benzyne-[2+2] Cycloaddition Cascade
    Ma, Zhi-Xiong
    Feltenberger, John B.
    Hsung, Richard P.
    [J]. ORGANIC LETTERS, 2012, 14 (11) : 2742 - 2745
  • [2] COMPETITIVE INTRAMOLECULAR [4+2] CYCLOADDITION AND [2+2] CYCLOADDITION OF SULFONYLALLENE
    KANEMATSU, K
    SUGIMOTO, N
    KAWAOKA, M
    YEO, S
    SHIRO, M
    [J]. TETRAHEDRON LETTERS, 1991, 32 (10) : 1351 - 1354
  • [3] Intramolecular ketenimine-ketenimine [2+2] and [4+2] cycloadditions
    Alajarin, Mateo
    Bonillo, Baltasar
    Sanchez-Andrada, Pilar
    Vidal, Angel
    Bautista, Delia
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (15): : 5863 - 5866
  • [4] EVIDENCE FOR [2+2] AND [4+2] CYCLOADDITIONS OF ALLYLIC GRIGNARD-REAGENTS TO BENZYNE
    DUBOUDIN, JG
    JOUSSEAUME, B
    PINET, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (13) : 454 - 455
  • [5] STEREOCHEMISTRY OF 2+2 AND 2+4 CYCLOADDITIONS OF BENZYNE
    JONES, M
    LEVIN, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (23) : 6411 - &
  • [6] SELECTIVITY IN INTRAMOLECULAR [4+2] AND [2+2] THERMAL CYCLOADDITIONS OF N-(PHENYLPROPARGYL) CINNAMAMIDES
    KLEMM, LH
    HWANG, YN
    MCGUIRE, TM
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1974, : 15 - 15
  • [7] PHOTOCHEMICAL [2+2]CYCLOADDITIONS AND [4+2]CYCLOADDITIONS OF N-METHYLPHTHALIMIDE TO ALLYLTRIMETHYLSILANE
    KUBO, Y
    TANIGUCHI, E
    ARAKI, T
    [J]. HETEROCYCLES, 1989, 29 (10) : 1857 - 1860
  • [8] [2+2]CYCLOADDITIONS .2. [2+2]-CYCLOADDITION OF ALKYNES TO ALKENES
    LUKAS, JH
    BAARDMAN, F
    KOUWENHOVEN, AP
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (06): : 369 - 370
  • [9] Cycloaddition of Benzyne to Armchair Single-Walled Carbon Nanotubes: [2+2] or [4+2]?
    Yang, Tao
    Zhao, Xiang
    Nagase, Shigeru
    [J]. ORGANIC LETTERS, 2013, 15 (23) : 5960 - 5963
  • [10] INTRAMOLECULAR [2+2] CYCLOADDITION AND SEQUENTIAL RING EXPANSION
    ZHANG, W
    COLLINS, MR
    MAHMOOD, K
    DOWD, P
    [J]. TETRAHEDRON LETTERS, 1995, 36 (16) : 2729 - 2732
12345