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
  • [31] Ruthenium-Catalyzed Multicomponent Reactions: Access to -Silyl--Hydroxy Vinylsilanes, Stereodefined 1,3-Dienes, and Cyclohexenes
    Trost, Barry M.
    Koester, Dennis C.
    Sharif, Ehesan U.
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (08) : 2634 - 2638
  • [32] Ruthenium-catalyzed two-component addition to form 1,3-dienes: Optimization, scope, applications, and mechanism
    Trost, BM
    Pinkerton, AB
    Seidel, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (50) : 12466 - 12476
  • [33] Boron-directed regio- and stereoselective enyne cross metathesis: Efficient synthesis of vinyl boronate containing 1,3-dienes
    Kim, M
    Lee, D
    ORGANIC LETTERS, 2005, 7 (09) : 1865 - 1868
  • [34] Palladium-Catalyzed Regio- and Enantioselective Hydrosulfonylation of 1,3-Dienes with Sulfinic Acids: Scope, Mechanism, and Origin of Selectivity
    Zhang, Qinglong
    Dong, Dongfang
    Zi, Weiwei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (37) : 15860 - 15869
  • [35] Highly Regio- and Enantioselective Copper-Catalyzed Reductive Hydroxymethylation of Styrenes and 1,3-Dienes with CO2
    Yu, Da-Gang (dgyu@scu.edu.cn), 1600, American Chemical Society (139):
  • [36] Highly Regio- and Enantioselective Copper-Catalyzed Reductive Hydroxymethylation of Styrenes and 1,3-Dienes with CO2
    Gui, Yong-Yuan
    Hu, Naifu
    Chen, Xiao-Wang
    Liao, Li-Li
    Ju, Tao
    Ye, Jian-Heng
    Zhang, Zhen
    Li, Jing
    Yu, Da-Gang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (47) : 17011 - 17014
  • [37] Mechanistic study of the Ni-catalyzed hydroalkylation of 1,3-dienes: The origins of regio- and enantioselectivities and a further rational design
    Bai, Yuna
    Xian, Anmei
    Yang, Xing
    Zhou, Ming
    Zhao, Xuefei
    Zhao, Lili
    JOURNAL OF COMPUTATIONAL CHEMISTRY, 2024, 45 (10) : 610 - 621
  • [38] Regio- and stereoselective Ni-catalyzed 1,4-hydroboration and diboration of 1,3-dienes: Access to stereodefined (Z)-allylboron reagents and derived allylic alcohols
    Ely, Robert J.
    Yu, Zhiyong
    Morken, James P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [39] Regio-, Site-, and Stereoselective Three-Component Aminofluorination of 1,3-Dienes via Cooperative Silver Salt and Copper Catalysis
    Li, Yang
    Dong, Yujiao
    Wang, Xin
    Li, Guangfu
    Xue, Huiqing
    Xin, Wanyang
    Zhang, Qian
    Guan, Wei
    Fu, Junkai
    ACS CATALYSIS, 2023, 13 (04) : 2410 - 2421
  • [40] Chemo-, Regio-, and Stereoselective cis-Hydroboration of 1,3-Enynes: Copper-Catalyzed Access to (Z,Z)- and (Z,E)-2-Boryl-1,3-dienes
    Buchbinder, Nicklas W.
    Nguyen, Long H.
    Beck, Owen N.
    Bage, Andrew D.
    Slebodnick, Carla
    Santos, Webster L.
    ORGANIC LETTERS, 2024, 26 (29) : 6136 - 6141
12345