Steric promotion of the intramolecular Pauson-Khand reaction of aryl enynes

被引:6
|
作者
Madu, Christian E. [1 ]
Lovely, Carl J. [1 ]
机构
[1] Univ Texas, Dept Chem & Biochem, Arlington, TX 76019 USA
关键词
organometallic; substituent effects; cyclization; stereoselectivity; cobalt-alkyne complexes; MEDIUM-SIZED RINGS; CONSTRUCTION; CHEMISTRY; NICHOLAS; CATIONS;
D O I
10.1055/s-2007-984880
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The intramolecular Pauson-Khand reaction of 1,8-enynes derived from salicylaldehyde derivatives has been investigated. Substrates derived from salicylaldehyde itself reacted poorly in this reaction, but related substrates containing ortho-tert-butyl substituents participated quite effectively and in many cases the cyclizations proceeded with high levels of diastereoselectivity.
引用
收藏
页码:2011 / 2016
页数:6
相关论文
共 50 条
  • [1] Steric buttressing in the Pauson-Khand reactions of aryl enynes
    Madu, Christian E.
    Seshadri, Hernalatha
    Lovely, Carl J.
    TETRAHEDRON, 2007, 63 (23) : 5019 - 5029
  • [2] Pauson-Khand reaction of aryl enynes.
    Lovely, CJ
    Seshadri, H
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U100 - U100
  • [3] Aromatic enynes as substrates for the intramolecular Pauson-Khand reaction
    Blanco-Urgoiti, J
    Casarrubios, L
    Pérez-Castells, J
    TETRAHEDRON LETTERS, 1999, 40 (14) : 2817 - 2820
  • [4] Intramolecular Pauson-Khand reactions of aromatic enynes
    Lovely, CJ
    Seshadri, H
    SYNTHETIC COMMUNICATIONS, 2001, 31 (16) : 2479 - 2490
  • [5] Steric buttressing in the Pauson-Khand reactions of benzyl enynes
    Madu, Christian E.
    Dias, H. V. Rasika
    Lovely, Carl J.
    TETRAHEDRON, 2017, 73 (43) : 6118 - 6137
  • [6] Scope and limitation of intramolecular Pauson-Khand reaction of fluorine-containing enynes
    Ishizaki, M
    Suzuki, D
    Hoshino, O
    JOURNAL OF FLUORINE CHEMISTRY, 2001, 111 (01) : 81 - 90
  • [7] Steric acceleration of the Pauson-Khand reaction.
    Lovely, CJ
    Madu, CE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U28 - U28
  • [8] CATALYTIC VERSION OF THE INTRAMOLECULAR PAUSON-KHAND REACTION
    JEONG, N
    HWANG, SH
    LEE, YS
    CHUNG, YK
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) : 3159 - 3160
  • [9] STERIC VS ELECTRONIC EFFECTS IN THE PAUSON-KHAND REACTION
    KRAFFT, ME
    ROMERO, RH
    SCOTT, IL
    SYNLETT, 1995, (05) : 577 - 578
  • [10] Rhodium-catalyzed intramolecular Pauson-Khand reaction
    Koga, Y
    Kobayashi, T
    Narasaka, K
    CHEMISTRY LETTERS, 1998, (03) : 249 - 250