Direct condensation of functionalized sp3 carbons with formanilides for enamine synthesis using an in situ generated HMDS amide catalyst

被引：26

作者：

Taneda, Hiroshi ^{[1
]}

Inamoto, Kiyofumi ^{[1
]}

Kondo, Yoshinori ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 49期

基金：

日本学术振兴会;

关键词：

EFFICIENT; ACID; DERIVATIVES; ESTERS; AGENTS;

D O I：

10.1039/c4cc02228a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The efficient synthesis of functionalized enamines including beta-enaminoesters was effectively accomplished by the direct condensation of functionalized sp(3) carbanions such as acetates with formamides using in situ generated HMDS base from catalytic cesium fluoride and stoichiometric tristrimethylsilylamine.

引用

页码：6523 / 6525

页数：3

共 39 条

[11] Erbium(III) triflate: A valuable catalyst for the synthesis of aldimines, ketimines, and enaminones
Dalpozzo, R
De Nino, A
Nardi, M
Russo, B
Procopio, A
[J]. SYNTHESIS-STUTTGART, 2006, (07): : 1127 - 1132
[12] Non-steroidal anti-inflammatory agents. Part 23 - Synthesis and pharmacological activity of enaminones which inhibit both bovine cyclooxygenase and 5-lipoxygenase
Dannhardt, G
Bauer, A
Nowe, U
[J]. JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1998, 340 (03): : 256 - 263
[13] Synthesis of enamines, enol ethers and related compounds by cross-coupling reactions
Dehli, JR
Legros, J
Bolm, C
[J]. CHEMICAL COMMUNICATIONS, 2005, (08) : 973 - 986
[14] Recent developments in the chemistry of enaminones
Elassar, AZA
El-Khair, AA
[J]. TETRAHEDRON, 2003, 59 (43) : 8463 - 8480
[15] Ytterbium triflate catalyzed synthesis of β-enaminones
Epifano, Francesco
Genovese, Salvatore
Curini, Massimo
[J]. TETRAHEDRON LETTERS, 2007, 48 (15) : 2717 - 2720
[16] Synthesis of N-substituted pyrrole and tetrahydroindole derivatives from alkenyl β-dicarbonyl compounds
Ferraz, HMC
Pereira, FLC
Leite, FS
Nunes, MRS
Payret-Arrúa, ME
[J]. TETRAHEDRON, 1999, 55 (36) : 10915 - 10924
[17] GREENHILL JV, 1977, CHEM SOC REV, V6, P277, DOI 10.1039/cs9770600277
[18] Copper-mediated synthesis of N-acyl vinylogous carbamic acids and derivatives:: Synthesis of the antibiotic CJ-15,801
Han, C
Shen, RC
Su, S
Porco, JA
[J]. ORGANIC LETTERS, 2004, 6 (01) : 27 - 30
[19] One-step deprotonation route to zinc amide and ester enolates for use in aldol reactions and Negishi couplings
Hlavinka, Mark L.
Hagadorn, John R.
[J]. TETRAHEDRON LETTERS, 2006, 47 (29) : 5049 - 5053
[20] Organocatalytic functionalization of heteroaromatic N-oxides with C-nucleophiles using in situ generated onium amide bases
Inamoto, Kiyofumi
Araki, Yuta
Kikkawa, Shoko
Yonemoto, Misato
Tanaka, Yoshiyuki
Kondo, Yoshinori
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (27) : 4438 - 4441

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