A novel ring-opening reaction of methylenecyclopropanes with aromatic amines catalyzed by Lewis acids

被引：57

作者：

Shi, M

Chen, Y

Xu, B

Tang, J

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

[2] E China Normal Univ, Dept Chem, Shanghai 200062, Peoples R China

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 45期

基金：

中国国家自然科学基金;

关键词：

methylenecyclopropanes (MCPs); aromatic amines; aliphatic amines; ring-opening reactions Lewis acids;

D O I：

10.1016/S0040-4039(02)01984-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methylenecyclopropanes (MCPs) can react with aromatic amines to give the corresponding homoallylic amines in good to high yields in the presence of Lewis acids. The substituents on the benzene ring of the MCPs or the aromatic amines can affect significantly the reaction rate. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：8019 / 8024

页数：6

相关论文

共 22 条

[11] Transition metal-mediated cycloaddition reactions [J].

Lautens, M ;

Klute, W ;

Tam, W .

CHEMICAL REVIEWS, 1996, 96 (01) :49-92

[12] Metal-initiated amination of alkenes and alkynes [J].

Muller, TE ;

Beller, M .

CHEMICAL REVIEWS, 1998, 98 (02) :675-703

[13] Ring opening in the hydroamination of methylenecyclopropanes catalyzed by palladium [J].

Nakamura, I ;

Itagaki, H ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6458-6459

[14]

Nakamura I, 2001, ANGEW CHEM INT EDIT, V40, P1298, DOI 10.1002/1521-3773(20010401)40:7<1298::AID-ANIE1298>3.0.CO

[15]

2-4

[16] Palladium-catalyzed [3+2] cycloaddition of alkylidenecyclopropanes with imines [J].

Oh, BH ;

Nakamura, I ;

Saito, S ;

Yamamoto, Y .

TETRAHEDRON LETTERS, 2001, 42 (35) :6203-6205

[17]

SAVOIA D, 1995, METHODS ORGANIC CH E, V21, P5356

[18] Lewis acid-catalyzed ring-opening reactions of methylenecyclopropanes with alcoholic or acidic nucleophiles [J].

Shi, M ;

Xu, B .

ORGANIC LETTERS, 2002, 4 (13) :2145-2148

[19] Palladium- and platinum-catalyzed silaboration of methylenecyclopropanes through selective proximal or distal C-C bond cleavage [J].

Suginome, M ;

Matsuda, T ;

Ito, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) :11015-11016

[20] Inter- and intramolecular palladium-catalyzed hydrocarbonation of methylenecyclopropanes with carbon pronucleophiles [J].

Tsukada, N ;

Shibuya, A ;

Nakamura, I ;

Kitahara, H ;

Yamamoto, Y .

TETRAHEDRON, 1999, 55 (29) :8833-8844