A facile synthesis of β-allenyl furanimines via Pd-catalyzed cyclization of 2,3-allenamides with propargylic carbonates

被引：11

作者：

Chen, Guofei ^{[1
]}

Zhang, Ya ^{[1
]}

Fu, Chunling ^{[1
]}

Ma, Shengming ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Lab Mol Recognit & Synth, Hangzhou 310027, Zhejiang, Peoples R China

来源：

TETRAHEDRON | 2011年 / 67卷 / 12期

基金：

中国国家自然科学基金;

关键词：

2,3-Allenamides; Propargylic carbonates; Pd-catalysis; Cyclization; EFFICIENT SYNTHESIS; COUPLING REACTION; PALLADIUM; HYDROXYLATION; HETEROCYCLES; ALCOHOLS;

D O I：

10.1016/j.tet.2011.01.041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Pd(OAc)(2)/TFP-catalyzed cyclization reaction of 2,3-allenamides in the presence of propargylic carbonates provides an efficient route to beta-allenyl furanimine derivatives. Preliminary mechanistic study showed that this reaction was probably initiated by Pd(0) species. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2332 / 2337

页数：6

共 32 条

[1] Homodimeric coupling-cyclization reaction of 2,3-allenamides
Chen, Guofei
Li, Yong
Fu, Chunling
Ma, Shengming
[J]. TETRAHEDRON, 2009, 65 (23) : 4547 - 4550
[2] Palladium-catalyzed regioselective coupling of propargylic substrates with terminal alkynes. Application to the synthesis of 1,2-dien-4-ynes
Condon-Gueugnot, S
Linstrumelle, C
[J]. TETRAHEDRON, 2000, 56 (13) : 1851 - 1857
[3] DARCEL C, 1994, SYNLETT, P457
[4] Darcel C, 1996, SYNLETT, P218
[5] Synthesis and properties of allenic natural products and pharmaceuticals
Hoffmann-Röder, A
Krause, N
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (10) : 1196 - 1216
[6] PALLADIUM-CATALYZED PROPARGYLIC VS ALLYLIC ALKYLATION
KEINAN, E
BOSCH, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (21) : 4006 - 4016
[7] Krause N., 2004, MODERN ALLENE CHEM, V1
[8] Krishna SH, 2002, TETRAHEDRON-ASYMMETR, V13, P2693
[9] Landor S.R., 1982, CHEM ALLENES, V1
[10] Ma SM, 2007, ALDRICHIM ACTA, V40, P91

← 1 2 3 4 →