Regio- and stereoselective ruthenium-catalyzed hydrovinylation of 1,3-dienes:: Application to the generation of a 20(S) steroidal side chain

被引：44
|
作者：
He, ZJ [1 ]
Yi, CS [1 ]
Donaldson, WA [1 ]
机构：
[1] Marquette Univ, Dept Chem, Milwaukee, WI 53201 USA
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 09期
关键词：
D O I：
10.1021/ol030031+
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The addition of ethylene to 1,3-dienes and 1-vinylcycloalkenes, catalyzed by two ruthenium complexes, proceeds in a regioselective fashion to afford 3-methyl-1,4-dienes as products. For a steroidal-based 1-vinylcycloalkene, the addition is stereospecific, giving a product with a 20(S) configuration.
引用
收藏
页码：1567 / 1569
页数：3
相关论文
共 50 条
  • [21] Addition of Dissimilar Carbenes across an Unsymmetrically Substituted Alkyne: Regio- and Stereoselective Synthesis of Trisubstituted 1,3-Dienes
    O'Connor, Joseph M.
    Chen, Ming-Chou
    Holland, Ryan L.
    Rheingold, Arnold L.
    ORGANOMETALLICS, 2011, 30 (03) : 369 - 371
  • [22] Regio- and Stereoselective Synthesis of 2-Amino-1,3-diene Derivatives by Ruthenium-Catalyzed Coupling of Ynamides and Ethylene
    Saito, Nozomi
    Saito, Keiichi
    Shiro, Motoo
    Sato, Yoshihiro
    ORGANIC LETTERS, 2011, 13 (10) : 2718 - 2721
  • [23] Regio- and Stereoselective Synthesis of Enynyl Boronates via Ruthenium-Catalyzed Hydroboration of 1,4-Diaryl-Substituted 1,3-Diynes
    Sokolnicki, Tomasz
    Szyling, Jakub
    Franczyk, Adrian
    Walkowiak, Jedrzej
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (01) : 177 - 183
  • [24] Cobalt-Catalyzed Regio-, Diastereo- and Enantioselective Intermolecular Hydrosilylation of 1,3-Dienes with Prochiral Silanes
    Wang, Lei
    Lu, Wenxin
    Zhang, Jiwu
    Chong, Qinglei
    Meng, Fanke
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (30)
  • [25] PALLADIUM-CATALYZED STEREOSELECTIVE HYDROVINYLATION OF DISUBSTITUTED ACETYLENES - PREPARATION OF FUNCTIONALIZED 1,2,4-TRISUBSTITUTED-1,3-DIENES
    ARCADI, A
    BERNOCCHI, E
    BURINI, A
    CACCHI, S
    MARINELLI, F
    PIETRONI, B
    TETRAHEDRON LETTERS, 1989, 30 (26) : 3465 - 3468
  • [26] Hydrovinylation of 1,3-dienes: A new protocol, an asymmetric variation, and a potential solution to the exocyclic side chain stereochemistry problem
    Zhang, Aibin
    RajanBabu, T.V.
    Journal of the American Chemical Society, 2006, 128 (01): : 54 - 55
  • [27] Regio- and Stereoselective Ni-Catalyzed 1,4-Hydroboration of 1,3-Dienes: Access to Stereodefined (Z)-Allylboron Reagents and Derived Allylic Alcohols
    Ely, Robert J.
    Morken, James P.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (08) : 2534 - +
  • [28] Hydrovinylation of 1,3-dienes: A new protocol, an asymmetric variation, and a potential solution to the exocyclic side chain stereochemistry problem
    Zhang, AB
    RajanBabu, TV
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) : 54 - 55
  • [29] Ligand tuning in asymmetric hydrovinylation of 1,3-dienes: A stereoselective route to either steroid-C20 (S) or -C20 (R) derivatives
    Saha, Biswajit
    Smith, Craig R.
    RajanBabu, T.V.
    Journal of the American Chemical Society, 2008, 130 (28): : 9000 - 9005
  • [30] Ligand tuning in asymmetric hydrovinylation of 1,3-dienes:: A stereoselective route to either steroid-C20 (S) or -C20 (R) derivatives
    Saha, Biswajit
    Smith, Craig R.
    RajanBabu, T. V.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) : 9000 - 9005
12345