Reductive lithiation of 1,3-dimethyl-2-arylimidazolidines

被引：5

作者：

Azzena, U ^{[1
]}

Dettori, G ^{[1
]}

Pisano, L ^{[1
]}

Siotto, I ^{[1
]}

机构：

[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

来源：

TETRAHEDRON | 2005年 / 61卷 / 13期

关键词：

aromatic aldehydes; lithiation; protective groups; reduction;

D O I：

10.1016/j.tet.2005.01.093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Naphthalene catalyzed lithiation of 1,3-dimethyl-2-phenylimidazolidine led to cleavage of the benzylic carbon-nitrogen bond, with formation of an intermediate dianion. Under similar conditions, 1,3-dimethyl-2-(4-chlorophenyl)imidazolidine underwent regioselective cleavage of the aromatic carbon-chlorine bond, leading to a 4-formylphenyllithium equivalent, whilst 1,3-dimethyl-2-(4-methoxymethylphenyl)imidazolidine underwent regioselective cleavage of the benzylic carbon-oxygen bond, leading to a 4-formylbenzyllithium equivalent. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3177 / 3182

页数：6

共 25 条

[1] Nitrogen-containing remote functionalised organolithium compounds by reductive opening of five- and six-membered heterocycles [J].

Almena, J ;

Foubelo, F ;

Yus, M .

TETRAHEDRON, 1996, 52 (25) :8545-8564

[2] 1,2-DI(LITHIOMETHYL)BENZENE FROM PHTHALAN - SEQUENTIAL INTRODUCTION OF 2 DIFFERENT ELECTROPHILES [J].

ALMENA, J ;

FOUBELO, F ;

YUS, M .

TETRAHEDRON, 1995, 51 (11) :3351-3364

[3] Reductive opening of thiophthalan: A new route to functionalized sulfur-containing compounds [J].

Almena, J ;

Foubelo, F ;

Yus, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1859-1862

[4] Diastereoselective electrophilic substitution of γ-oxy-substituted benzyllithiums [J].

Arrica, MA ;

Azzena, U ;

Pilo, L ;

Piras, E .

TETRAHEDRON LETTERS, 2002, 43 (29) :5137-5139

[5] Alkali metal-mediated synthesis of 1-and 4-substituted N-alkyl-1,2,3,4-tetrahydroisoquinolines [J].

Azzena, U ;

Pisano, L ;

Pittalis, M .

HETEROCYCLES, 2004, 63 (02) :401-409

[6] Practical generation of 3,5-dimethoxybenzyllithium: application to the synthesis of 5-substituted-resorcinols [J].

Azzena, U ;

Dettori, G ;

Idini, MV ;

Pisano, L ;

Sechi, G .

APPLIED ORGANOMETALLIC CHEMISTRY, 2003, 17 (11) :851-855

[7] Diastereoselective electrophilic substitution of α-amino-substituted benzylic organometallics [J].

Azzena, U .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (03) :360-365

[8] Electron-transfer-induced reductive cleavage of phthalans: Reactivity and synthetic applications [J].

Azzena, U ;

Demartis, S ;

Melloni, G .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :4913-4919

[9] Reductive cleavage of benzannelated cyclic ethers and amines: Synthetic applications [J].

Azzena, U ;

Demartis, S ;

Pilo, L ;

Piras, E .

TETRAHEDRON, 2000, 56 (42) :8375-8382

[10] Reductive lithiation of arylalkyl methyl ethers [J].

Azzena, U ;

Carta, S ;

Melloni, G ;

Sechi, A .

TETRAHEDRON, 1997, 53 (47) :16205-16212

← 1 2 3 →