Synthesis of β-Amino acids via catalyst- and solvent-free aza-Michael reaction

被引：19

作者：

Zou Bo ^{[1
]}

Jiang Huan-Feng ^{[1
]}

机构：

[1] S China Univ Technol, Coll Chem, Guangzhou 510640, Guangdong, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2008年 / 26卷 / 07期

关键词：

aza-Michael addition; catalyst-free; solvent-free; alpha; beta-unsaturated compound; beta-amino acid;

D O I：

10.1002/cjoc.200890238

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A safe, environmentally friendly and cost-effective method for the synthesis of beta-amino acid derivatives has been developed. Treatment of alpha,beta-unsaturated compounds with aliphatic amines furnishes beta-amino acid derivatives in good to excellent yields via a catalyst- and solvent-free aza-Michael addition.

引用

页码：1309 / 1314

页数：6

共 46 条

[1]

Abele S, 2000, EUR J ORG CHEM, V2000, P1

[2] DUAL REACTIVITY OF 3,3-DIMETHOXYCYCLOPROPENE [J].

ALBERT, RM ;

BUTLER, GB .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (04) :674-679

[3] Fast, easy, solvent-free, microwave-promoted Michael addition of anilines to α,β-unsaturated alkenes:: synthesis of N-aryl functionalized β-amino esters and acids [J].

Amore, Kristen M. ;

Leadbeater, Nicholas E. ;

Miller, Tyson A. ;

Schmink, Jason R. .

TETRAHEDRON LETTERS, 2006, 47 (48) :8583-8586

[4]

[Anonymous], 1994, Aldrichimica Acta

[5]

ATSUBARA M, 1994, CHEM LETT, P827

[6] LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions [J].

Azizi, N ;

Saidi, MR .

TETRAHEDRON, 2004, 60 (02) :383-387

[7] Improved heteroatom nucleophilic addition to electron-poor alkenes promoted by CeCl3•7H2O/NaI system supported on alumina in solvent-free conditions [J].

Bartoli, G ;

Bartolacci, M ;

Giuliani, A ;

Marcantoni, E ;

Massaccesi, M ;

Torregiani, E .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :169-174

[8] Conjugate addition of amines to α,β-enones promoted by CeCl3•7H2O-NaI system supported in silica gel [J].

Bartoli, G ;

Bosco, M ;

Marcantoni, E ;

Petrini, M ;

Sambri, L ;

Torregiani, E .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :9052-9055

[9] Synthesis of β-amino esters via aza-Michael addition of amines to alkenes promoted on silica:: A useful and recyclable surface [J].

Basu, B ;

Das, P ;

Hossain, I .

SYNLETT, 2004, (14) :2630-2632

[10] A NEW SYNTHESIS OF BOTH THE ENANTIOMERS OF 4-AMINO-3-HYDROXYBUTANOIC ACID (GABOB) AND MM2 CALCULATIONS FOR ROTAMERS OF THE INTERMEDIATE OXAZOLIDIN-2-ONES [J].

BONGINI, A ;

CARDILLO, G ;

ORENA, M ;

PORZI, G ;

SANDRI, S .

TETRAHEDRON, 1987, 43 (19) :4377-4383

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