pi-Allyl palladium methodology for selective deprotection of allylamines. Practical synthesis of secondary amines

被引：0

作者：

LemaireAudoire, S ^{[1
]}

Savignac, M ^{[1
]}

Dupuis, C ^{[1
]}

Genet, JP ^{[1
]}

机构：

[1] ECOLE NATL SUPER CHIM PARIS,CNRS,SYNTH ORGAN LAB,F-75231 PARIS,FRANCE

来源：

BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE | 1995年 / 132卷 / 11期

关键词：

allylamine; deallylation; sequential deprotection; pi-allyl palladium complexes; 2-mercaptobenzoic acid; substitution of amines;

D O I：

暂无

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The palladium-promoted deallylation of allylamines derived from primary and secondary amines is achieved with high to quantitative yield in the presence of 2-mercaptobenzoic acid as an allyl scavenger. This method was used for the sequential cleavage of diallylamines. A. synthetic application of this procedure is presented in the preparation of secondary amines from diallylamines.

引用

页码：1157 / 1166

页数：10

共 47 条

[1]

BACKVALL JE, 1985, J AM CHEM SOC, V107, P3676

[2] A NOVEL REGIODIVERGENT RESOLUTION REACTION MEDIATED BY A HOMOCHIRAL LITHIUM AMIDE BASE [J].

BAMBRIDGE, K ;

SIMPKINS, NS ;

CLARK, BP .

TETRAHEDRON LETTERS, 1992, 33 (52) :8141-8144

[3] ISOMERIZATION OF ALLYL ETHERS CATALYZED BY CATIONIC IRIDIUM COMPLEX [IR(CYCLO-OCTA-1,5-DIENE)(PMEPH2)2]PF6 - HIGHLY STEREOSELECTIVE ROUTE TO TRANS-PROPENYL ETHERS [J].

BAUDRY, D ;

EPHRITIKHINE, M ;

FELKIN, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (16) :694-695

[4]

BERNARD JM, Patent No. 24088

[5]

BERNARD JM, Patent No. 2690153

[6]

BERNSARD JM, Patent No. 2703687

[7] ISOMERIZATION AND CLEAVAGE OF ALLYL ETHERS OF CARBOHYDRATES BY TRANS-[PD(NH3)2CL2] [J].

BIEG, T ;

SZEJA, W .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1985, 4 (03) :441-446

[8] CLEAVAGE OF ALLYL ETHERS WITH PD-C [J].

BOSS, R ;

SCHEFFOLD, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (09) :558-559

[9]

BRESLOW R, 1987, J AM CHEM SOC, V109, P1814

[10] ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES [J].

CAIN, CM ;

COUSINS, RPC ;

COUMBARIDES, G ;

SIMPKINS, NS .

TETRAHEDRON, 1990, 46 (02) :523-544

← 1 2 3 4 5 →