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

被引：56

作者：

Basu, B ^{[1
]}

Das, P ^{[1
]}

Hossain, I ^{[1
]}

机构：

[1] Univ N Bengal, Dept Chem, Raja Rammohanpur 734430, W Bengal, India

来源：

SYNLETT | 2004年 / 14期

关键词：

aza-Michael addition; amines; conjugated alkenes; beta-amino esters; silica gel;

D O I：

10.1055/s-2004-834836

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A solvent-free protocol for the synthesis of beta-amino esters and nitrites has been developed via conjugate addition of amines to electron-deficient alkenes promoted oil silica. The silica surface may be recycled. Both aliphatic and aromatic primary or secondary airlines worked efficiently to yield the desired adducts ill good to excellent yields.

引用

页码：2630 / 2632

页数：3

共 30 条

[1] 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

[2] Microwave-assisted Suzuki coupling on a KF-alumina surface: synthesis of polyaryls [J].

Basu, B ;

Das, P ;

Bhuiyan, MMH ;

Jha, S .

TETRAHEDRON LETTERS, 2003, 44 (19) :3817-3820

[3] Palladium-catalysed amination of halopyridines on a KF-alumina surface [J].

Basu, B ;

Jha, S ;

Mridha, NK ;

Bhuiyan, MMH .

TETRAHEDRON LETTERS, 2002, 43 (44) :7967-7969

[4] CONJUGATED ADDITION OF PRIMARY AMINES TO ALPHA-(1-HYDROXYALKYL)ACRYLIC COMPOUNDS - NOVEL SYNTHESIS OF POLYFUNCTIONAL BETA-LACTAMS AND GAMMA-LACTAMS [J].

BENAYED, T ;

AMRI, H ;

ELGAIED, MM ;

VILLERAS, J .

TETRAHEDRON, 1995, 51 (35) :9633-9642

[5]

Bull SD, 2000, SYNLETT, P1257

[6] Asymmetric synthesis of beta-amino acids and alpha-substituted beta-amino acids [J].

Cardillo, G ;

Tomasini, C .

CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :117-&

[7] Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility [J].

Cave, GWV ;

Raston, CL ;

Scott, JL .

CHEMICAL COMMUNICATIONS, 2001, (21) :2159-2169

[8] HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF BETA-AMINO ACID-ESTERS AND BETA-LACTAMS FROM ACHIRAL ESTERS AND IMINES [J].

COREY, EJ ;

DECICCO, CP ;

NEWBOLD, RC .

TETRAHEDRON LETTERS, 1991, 32 (39) :5287-5290

[9]

DAS P, 2004, SYNTHETIC COMMUN, V34, P2184

[10]

DAVIES SG, 1995, SYNLETT, P700

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