Stereoselective Synthesis of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation of Ynamides

被引:134
|
作者
Gourdet, Benoit [1 ]
Lam, Hon Wai [1 ]
机构
[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland
关键词
COUPLING REACTIONS; CHIRAL ENAMIDES; TERMINAL ALKYNES; ALDEHYDES; CYCLOPROPANATION; NUCLEOPHILES; CHEMISTRY; REAGENTS; ETHERS;
D O I
10.1021/ja900946h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new rhodium-catalyzed carbozincation of ynamides has been developed, using diorganozinc: reagents or functionatized alkylzinc: halides. The reactions are highly regio- and stereoselective, allowing access to a wide range of multisubstituted enamides, which are increasingly important building blocks for organic synthesis. Utilization of the alkenylzinc intermediates in further carbon-carbon bond-forming reactions to form trisubstituted enamides is also possible.
引用
收藏
页码:3802 / +
页数:3
相关论文
共 50 条
  • [1] Preparation of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation and Hydrozincation of Ynamides
    Gourdet, Benoit
    Rudkin, Mairi E.
    Watts, Ciorsdaidh A.
    Lam, Hon Wai
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (20): : 7849 - 7858
  • [2] Synthesis of Multisubstituted Enamides via Pd-Catalyzed Chloroallylation of Ynamides
    Lu, Zenghui
    Kong, Wei
    Yuan, Zheliang
    Zhao, Xueyan
    Zhu, Gangguo
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (20): : 8524 - 8529
  • [4] Rhodium-catalyzed carbometalation of ynamides with organoboron reagents
    Gourdet, Benoit
    Smith, Donna L.
    Lam, Hon Wai
    TETRAHEDRON, 2010, 66 (32) : 6026 - 6031
  • [5] Rhodium-Catalyzed Regiodivergent and Enantioselective Hydroboration of Enamides
    Bai, Xiao-Yan
    Zhao, Wei
    Sun, Xin
    Li, Bi-Jie
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (50) : 19870 - 19878
  • [6] Regio- and Stereoselective Synthesis of Tri- and Tetrasubstituted Enamides via Palladium-Catalyzed Silaboration of Ynamides
    Saito, Nozomi
    Saito, Keiichi
    Sato, Hiroyasu
    Sato, Yoshihiro
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (05) : 853 - 856
  • [7] Rhodium-catalyzed asymmetric hydrogenation of β-branched enamides for the synthesis of β-stereogenic amines
    Zhang, Jian
    Liu, Chong
    Wang, Xingguang
    Chen, Jianzhong
    Zhang, Zhenfeng
    Zhang, Wanbin
    CHEMICAL COMMUNICATIONS, 2018, 54 (47) : 6024 - 6027
  • [8] Rhodium-Catalyzed Highly Regioselective and Stereoselective Intermolecular Hydrosilylation of Internal Ynamides under Mild Conditions
    Zheng, Nan
    Song, Wangze
    Zhang, Tiexin
    Li, Ming
    Zheng, Yubin
    Chen, Lingyue
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (11): : 6210 - 6216
  • [9] Rhodium-Catalyzed Annulation of Ynamides with Bifunctional Arylboron Reagents
    Gourdet, Benoit
    Rudkin, Mairi E.
    Lam, Hon Wai
    ORGANIC LETTERS, 2010, 12 (11) : 2554 - 2557
  • [10] Iron(II)/copper(I)-mediated stereoselective carbozincation of ynamides. One-pot synthesis of α-allyl-tetrasubstituted-enamides
    Lingua, Hugo
    Vibert, Francois
    Mouysset, Dominique
    Siri, Didier
    Bertrand, Michele P.
    Feray, Laurence
    TETRAHEDRON, 2017, 73 (25) : 3415 - 3422