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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 11期

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

页码：3802 / +

页数：3

共 50 条

[21] Rhodium-catalyzed Sommelet-Hauser type rearrangement of α-diazoimines: synthesis of functionalized enamides
Reddy, Angula Chandra Shekar
Ramachandran, Kuppan
Reddy, Palagulla Maheswar
Anbarasan, Pazhamalai
CHEMICAL COMMUNICATIONS, 2020, 56 (42) : 5649 - 5652
[22] Synthesis of Enantioenriched β-Hydroxy-γ-Acetal Enamides by Rhodium-Catalyzed Asymmetric Transfer Hydrogenation
Westermeyer, Anne
Guillamot, Gerard
Phansavath, Phannarath
Ratoyelomanana-Vidal, Virginie
ORGANIC LETTERS, 2020, 22 (10) : 3911 - 3914
[23] Ligand and substrate effects on the mechanism of rhodium-catalyzed hydrogenation of enamides
Donoghue, Patrick J.
Helquist, Paul
Wiest, Olaf
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (03): : 839 - 847
[24] Copper-Catalyzed Regio- and Stereoselective Hydrothiolation of Allenamides, Enamides, and Ynamides
Pages, Lucas
Bouquin, Maxime
Jaroschik, Florian
Monnier, Florian
Taillefer, Marc
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (02): : 1168 - 1176
[25] Synthesis of dialkoxydiphenylsilanes via the rhodium-catalyzed hydrosilylation of aldehydes
Nogues, Christophe
Argouarch, Gilles
TETRAHEDRON LETTERS, 2019, 60 (40)
[26] Rhodium-Catalyzed Oxidative Coupling of Aryl Hydrazones with Internal Alkynes: Efficient Synthesis of Multisubstituted Isoquinolines
Liu, Wenting
Hong, Xiaohu
Xu, Bin
SYNTHESIS-STUTTGART, 2013, 45 (15): : 2137 - 2149
[27] Rhodium-Catalyzed Asymmetric Cycloisomerization of 1,6-Ene-ynamides
Nishimura, Takahiro
Takiguchi, Yuka
Maeda, Yuko
Hayashi, Tamio
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (07) : 1374 - 1382
[28] A RHODIUM-CATALYZED SYNTHESIS OF PYRIDONES
FLYNN, ST
HASSOHENDERSON, SE
PARKINS, AW
JOURNAL OF MOLECULAR CATALYSIS, 1985, 32 (01): : 101 - 105
[29] Rhodium-Catalyzed Pyridylation of Alkynamides with Pyridylboronic Acids: A Route to Functionalized Enamides
Zhu, Huilong
Sun, Dingcheng
Zhang, Shengxiang
Chen, Junning
Xu, Zhou
CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (54)
[30] Ethanol as a Hydrogenating Agent: Palladium-Catalyzed Stereoselective Hydrogenation of Ynamides To Give Enamides
Reddy, Alla Siva
Swamy, K. C. Kumara
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (24) : 6984 - 6988

← 1 2 3 4 5 →