Indium- or zinc-mediated one-pot synthesis of homoallylamines, β-amino esters, and β-amino nitriles

被引：28

作者：

Choucair, B ^{[1
]}

Léon, H ^{[1
]}

Miré, MA ^{[1
]}

Lebreton, C ^{[1
]}

Mosset, P ^{[1
]}

机构：

[1] Ecole Natl Super Chim Rennes, Lab Synth & Activat Biomol, CNRS, ESA 6052, F-35700 Rennes, France

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 13期

关键词：

D O I：

10.1021/ol005912k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Homoallylamines, beta-amino esters, and beta-amino nitriles were obtained in a one pot synthesis directly from an aldehyde and a secondary amine such as dibenzylamine or diallylamine. Their condensation with titanium(IV) isopropoxide generates an intermediate aminoalkoxy titanium complex. Further reaction in THF with nucleophilic organometallic species, generated in situ from indium or zinc and a reactive halide (allyl bromide, alkyl bromo- or iodoacetate, iodoacetonitrile), furnished the corresponding amines.

引用

页码：1851 / 1853

页数：3

共 17 条

[1]

Akiyama T, 1998, SYNLETT, P273

[2] INDIUM-MEDIATED ALLYLATION OF ALDIMINES [J].

BEUCHET, P ;

LEMARREC, N ;

MOSSET, P .

TETRAHEDRON LETTERS, 1992, 33 (40) :5959-5960

[3] TITANIUM(IV) ISOPROPOXIDE AND SODIUM-BOROHYDRIDE - A REAGENT OF CHOICE FOR REDUCTIVE AMINATION [J].

BHATTACHARYYA, S .

TETRAHEDRON LETTERS, 1994, 35 (15) :2401-2404

[4] REDUCTIVE ALKYLATIONS OF DIMETHYLAMINE USING TITANIUM(IV) ISOPROPOXIDE AND SODIUM-BOROHYDRIDE - AN EFFICIENT, SAFE, AND CONVENIENT METHOD FOR THE SYNTHESIS OF N,N-DIMETHYLATED TERTIARY-AMINES [J].

BHATTACHARYYA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4928-4929

[5] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[6]

CINTAS P, 1995, SYNLETT, P1087

[7] REACTIONS OF ALLYLSTANNANES WITH INSITU GENERATED IMMONIUM SALTS IN PROTIC SOLVENT - A FACILE AMINOMETHANO DESTANNYLATION PROCESS [J].

GRIECO, PA ;

BAHSAS, A .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) :1378-1380

[8]

Kleinman E. F., 1991, COMPREHENSIVE ORGANI, V2, P975

[9] Sc(OTf)3-catalyzed three-component reactions of aldehydes, amines and allyltributylstannane in micellar systems.: Facile synthesis of homoallylic amines in water [J].

Kobayashi, S ;

Busujima, T ;

Nagayama, S .

CHEMICAL COMMUNICATIONS, 1998, (01) :19-20

[10] Synthesis of sterically hindered esters via titanium catalyzed transesterification [J].

Krasik, P .

TETRAHEDRON LETTERS, 1998, 39 (24) :4223-4226

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