Enamines in solid-phase:: synthesis and reactivity towards electrophiles

被引：10

作者：

Aznar, F ^{[1
]}

Valdés, C ^{[1
]}

Cabal, MP ^{[1
]}

机构：

[1] Univ Oviedo, Inst Quim Organomet Enrique Moles, Unidad Asociada, CSIC, E-33071 Oviedo, Spain

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(00)00946-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enamines are synthesized in solid-phase by amination of terminal acetylenes with a secondary amine attached to Wang resin in a process catalyzed by mercury(II) acetate. The enamines obtained react with electrophiles such as isocyanates and nitroolefins to give rise to the expected addition products, which can be released from the resin by hydrolysis of the enamine under mild acidic conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5683 / 5687

页数：5

共 13 条

[1]

Balkenhohl F, 1996, ANGEW CHEM INT EDIT, V35, P2289

[2] Cycloaddition reactions of chiral 2-amino-1,3-butadienes with nitroalkenes: Synthesis of enantiomerically pure 4-nitrocyclohexanones [J].

Barluenga, J ;

Aznar, F ;

Ribas, C ;

Valdes, C .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6746-6753

[3] CATALYTIC AMINOMERCURATION REACTIONS OF 3-ALKEN-1-YNES - AN IMPROVED METHOD FOR THE SYNTHESIS OF 2-AMINO-1,3-BUTADIENES AND 1-AZA-1,3-BUTADIENES [J].

BARLUENGA, J ;

AZNAR, F ;

VALDES, C ;

CABAL, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6166-6171

[4] CATALYTIC AND NON-CATALYTIC ADDITION OF AROMATIC-AMINES TO TERMINAL ACETYLENES IN THE PRESENCE OF MERCURY(II) CHLORIDE AND ACETATE [J].

BARLUENGA, J ;

AZNAR, F ;

LIZ, R ;

RODES, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (12) :2732-2737

[5]

Blackburn C, 1998, BIOPOLYMERS, V47, P311, DOI 10.1002/(SICI)1097-0282(1998)47:5<311::AID-BIP2>3.0.CO

[6]

2-V

[7]

Brown RCD, 1998, J CHEM SOC PERK T 1, P3293

[8]

Cook A. G., 1988, ENAMINES

[9]

COREY EJ, 1972, TETRAHEDRON LETT, P3769

[10] Solid phase synthesis of 2-aminobutadienes using a piperazine linker [J].

Hird, NW ;

Irie, K ;

Nagai, K .

TETRAHEDRON LETTERS, 1997, 38 (40) :7111-7114

← 1 2 →