Rhodium-catalyzed tandem cyclization-cycloaddition reactions of enynebenzaldehydes: construction of polycyclic ring systems

被引：88
|
作者：
Shin, S [1 ]
Gupta, AK [1 ]
Rhim, CY [1 ]
Oh, CH [1 ]
机构：
[1] Hanyang Univ, Dept Chem, Seoul 133791, South Korea
来源：
CHEMICAL COMMUNICATIONS | 2005年 / 35期
关键词：
D O I：
10.1039/b506003f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
o-(1,6-Enynyl)benzaldehydes underwent a novel mode of cycloaddition using Rh(I)-precatalyst, via [3 + 2] cycloaddition of presumed dipolar carbonyl ylide intermediate generated by Rh-catalyst and the utility of this mechanistically intriguing enyne cyclization can be found in a number of polycyclic natural product skeletons.
引用
收藏
页码：4429 / 4431
页数：3
相关论文
共 50 条
  • [21] Divergent Rhodium-Catalyzed Cyclization Reactions of Enoldiazoacetamides with Nitrosoarenes
    Cheng, Qing-Qing
    Lankelma, Marianne
    Wherritt, Daniel
    Arman, Hadi
    Doyle, Michael P.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (29) : 9839 - 9842
  • [22] Gold-Catalyzed Cyclization-Cycloaddition Cascade Reactions of Allenyl Acetals with Nitrones
    Vasu, Dhananjayan
    Liu, Rai-Shung
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (43) : 13638 - 13641
  • [23] An approach toward the illudin family of sesquiterpenes using the tandem cyclization-cycloaddition reaction of rhodium carbenoids
    Padwa, A
    Curtis, EA
    Sandanayaka, VP
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05): : 1317 - 1325
  • [24] Enantioselective palladium(II) catalyzed cyclization-cycloaddition cascade reactions of alkenyl oximes
    Abozeid, Mohamed A.
    Takizawa, Shinobu
    Sasai, Hiroaki
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [25] Rhodium carbenoid-induced tandem cyclization-cycloaddition approach toward the synthesis of pseudolaric acid A.
    Chiu, P
    Chen, B
    Cheng, KF
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U36 - U37
  • [26] Rhodium-catalyzed [5+2] cycloaddition reactions in water
    Wender, PA
    Love, JA
    Williams, TJ
    SYNLETT, 2003, (09) : 1295 - 1298
  • [27] Rhodium-Catalyzed Ring Expansion Reactions for the Concise Construction of Densely Functionalized Oxathionines and Oxathiocines
    Liu, Haitao
    Chen, Feng
    Zhao, Nannan
    Vummaleti, Sai V. C.
    Sullivan, Michael B.
    Ying, Jackie Y.
    Wang, Lei
    ACS CATALYSIS, 2022, 12 (13) : 7524 - 7530
  • [28] Application of a rhodium-catalyzed cyclization cycloaddition cascade strategy to the total synthesis of (-)-curcumol
    Zhang, X. X.
    Ko, R. Y. Y.
    Xie, X. Q.
    Qi, W. P.
    Li, P. C.
    Chiu, P.
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (07): : 1092 - 1095
  • [29] Tandem cyclization-cycloaddition behavior of rhodium carbenoids with carbonyl compounds: Stereoselective studies on the construction of novel epoxy-bridged tetrahydropyranone frameworks
    Muthusamy, S
    Babu, SA
    Gunanathan, C
    Ganguly, B
    Suresh, E
    Dastidar, P
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (23): : 8019 - 8033
  • [30] Application of a Rhodium-Catalyzed Addition/Cyclization Sequence toward the Synthesis of Polycyclic Heteroaromatics
    Tseng, Nai-Wen
    Lautens, Mark
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (04): : 1809 - 1811
12345