Allylpalladium umpolung in the three-component coupling synthesis of homoallylic amines

被引：32

作者：

Hopkins, Chad D. ^{[1
]}

Malinakova, Helena C. ^{[1
]}

机构：

[1] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 26期

关键词：

D O I：

10.1021/ol0624528

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Homoallylic amines and alpha-amino esters were prepared via a Pd(II)-catalyzed coupling of boronic acids and 1,2- nonadiene with ethyl iminoacetate or aliphatic, aromatic, and heteroaromatic imines. The allylpalladium umpolung was induced by a Pd( OAc)(2) catalyst with commercial phosphine ligands.

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页码：5971 / 5974

页数：4

相关论文

共 41 条

[11] Stereoselective synthesis of substituted N-heterocycles via sequential cross metathesis -: reductive cyclization [J].

Gebauer, J ;

Dewi, P ;

Blechert, S .

TETRAHEDRON LETTERS, 2005, 46 (01) :43-46

[12] Regiocontrolled, palladium-catalyzed bisfunctionalization of allenyl esters.: Multicomponent coupling approaches to highly substituted α,β-unsaturated δ-lactones [J].

Hopkins, CD ;

Guan, L ;

Malinakova, HC .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :6848-6862

[13] The total synthesis of eupomatilones 2 and 5 [J].

Kabalka, GW ;

Venkataiah, B .

TETRAHEDRON LETTERS, 2005, 46 (43) :7325-7328

[14] Allylation of aldehydes via Umpolung of π-allylpalladium(II) with triethylborane [J].

Kimura, M ;

Kiyama, I ;

Tomizawa, T ;

Horino, Y ;

Tanaka, S ;

Tamaru, Y .

TETRAHEDRON LETTERS, 1999, 40 (37) :6795-6798

[15]

Krause N., 2004, MODERN ALLENE CHEM

[16] ELECTROPHILIC SUBSTITUTION OF STRUCTURALLY RIGID ETA-1-ALLYLPALLADIUM COMPLEXES [J].

KUROSAWA, H ;

URABE, A .

CHEMISTRY LETTERS, 1985, (12) :1839-1840

[17] Synthesis and reactions of allylic, allenic, vinylic, and arylmetal reagents from halides and esters via transient organopalladium intermediates [J].

Marshall, JA .

CHEMICAL REVIEWS, 2000, 100 (08) :3163-3185

[18] The chemistry and pharmacology of tetrahydropyridines [J].

Mateeva, NN ;

Winfield, LL ;

Redda, KK .

CURRENT MEDICINAL CHEMISTRY, 2005, 12 (05) :551-571

[19] Nickel-catalyzed reductive coupling of alkynes and epoxides [J].

Molinaro, C ;

Jamison, TF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (27) :8076-8077

[20] Nickel-catalyzed reductive cyclizations and couplings [J].

Montgomery, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) :3890-3908

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