Indium(III) complex-catalyzed tandem carbonyl-ene reaction: An efficient construction of tetrahydropyran rings

被引：0
|
作者：
Loh, Teck-Peng [1 ]
Feng, Li-Chun [2 ]
Yang, Jian-Ying [1 ]
机构：
[1] Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
[2] Institute of Chemical Science, Ayer Rajah Crescent, Blk 28, 139959, Singapore
来源：
Synthesis | 2002年 / 07期
关键词：
Aldehydes; -; Hydrocarbons; Indium;
D O I：
10.1055/s-2002-28501
中图分类号：
学科分类号：
摘要：
An atom economic and efficient construction of tetrahydropyran rings using Indium triflate-catalyzed self-tandem carbonyl-ene, intramolecular (2,5) oxonium-ene cyclization between aldehydes and methylene cyclohexane is reported.
引用
收藏
页码：937 / 940
相关论文
共 50 条
  • [21] Intermolecular carbonyl-ene approach to the bicyclic analogues of enediyne antibiotics, neocarzinostatin, C-1027, and kedarcidin: Highly diastereoselective carbonyl-ene reaction with an alkyne-cobalt complex
    Mikami, K
    Feng, F
    Matsueda, H
    Yoshida, A
    Griersont, DS
    SYNLETT, 1996, (09) : 833 - &
  • [22] Scandium trifluoromethanesulfonate, an efficient catalyst for the intermolecular carbonyl-ene reaction and the intramolecular cyclisation of citronellal.
    Aggarwal, VK
    Vennall, GP
    Davey, PN
    Newman, C
    TETRAHEDRON LETTERS, 1998, 39 (14) : 1997 - 2000
  • [23] Lewis Acid-Catalyzed Carbonyl-Ene Reaction: Interplay between Aromaticity, Synchronicity, and Pauli Repulsion
    Rodriguez, Humberto A.
    Cruz, Daniel A.
    Padron, Juan I.
    Fernandez, Israel
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (15): : 11102 - 11110
  • [24] Ni-Catalyzed Formal Carbonyl-Ene Reaction of Terminal Alkenes via Carbon Dioxide Insertion
    Mori, Yasuyuki
    Shigeno, Chieko
    Luo, Ying
    Chan, Bun
    Onodera, Gen
    Kimura, Masanari
    SYNLETT, 2018, 29 (06) : 742 - 746
  • [25] A new asymmetric activation strategy for hydrazones as acyl anion equivalents in the bimetallic catalyzed carbonyl-ene reaction
    Hu, Wen-Bo
    Song, Xixi
    Wang, Min-Can
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (09) : 2055 - 2062
  • [26] Asymmetric carbonyl-ene reaction catalyzed by chiral N,N′-dioxide- nickel(II) complex: Remarkably broad substrate scope
    Zheng, Ke
    Shi, Jian
    Liu, Xiaohua
    Feng, Xiaoming
    Journal of the American Chemical Society, 2008, 130 (47): : 15770 - 15771
  • [27] Asymmetric Carbonyl-Ene Reaction Catalyzed by Chiral N,N′-Dioxide-Nickel(II) Complex: Remarkably Broad Substrate Scope
    Zheng, Ke
    Shi, Jian
    Liu, Xiaohua
    Feng, Xiaoming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (47) : 15770 - +
  • [28] Significant counterion effect of the In(III)-pybox complex in highly enantioselective carbonyl-ene reactions of ethyl glyoxylate
    Zhao, Jun-Feng
    Tjan, Teguh-Budiono W.
    Loh, Teck-Peng
    TETRAHEDRON LETTERS, 2010, 51 (43) : 5649 - 5652
  • [29] Rhodium complex-catalyzed reaction of isonitriles with carbonyl compounds: Catalytic synthesis of pyrroles
    Takaya, H
    Kojima, S
    Murahashi, SI
    ORGANIC LETTERS, 2001, 3 (03) : 421 - 424
  • [30] Enantio- and Diastereoselective Carbonyl-Ene Cyclization-Acetalization Tandem Reaction Catalyzed by Tris(pentafluorophenyl)borane-Assisted Chiral Phosphoric Acids
    Ishihara, Hideyuki
    Huang, Jianhao
    Mochizuki, Takuya
    Hatano, Manabu
    Ishihara, Kazuaki
    ACS CATALYSIS, 2021, 11 (10) : 6121 - 6127
12345