Synthesis of aromatic (E)- or (Z)-α,β-unsaturated amides with total or very high selectivity from α,β-epoxyamides and samarium diiodide

被引：32

作者：

Concellón, JM ^{[1
]}

Bardales, E ^{[1
]}

机构：

[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 24期

关键词：

D O I：

10.1021/jo0349577

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly stereoselective synthesis of aromatic alpha,beta-unsaturated amides was achieved by treatment of aromatic alpha,beta-epoxyamides with samarium diiodide. The starting compounds 1 and 3 are easily prepared by the reaction of enolates derived from alpha-chloroamides with carbonyl compounds at -78 degreesC. A mechanism to explain this transformation is proposed.

引用

页码：9492 / 9495

页数：4

共 45 条

[1] CONJUGATE ADDITION OF ORGANO-LITHIUM REAGENTS TO ACRYLANILIDE ANIONS [J].

BALDWIN, JE ;

DUPONT, WA .

TETRAHEDRON LETTERS, 1980, 21 (19) :1881-1882

[2]

Bauer, 1995, HOUBEN WEYL STEREO C, V21, P2735

[3] SYNTHESIS OF BIOLOGICALLY-ACTIVE UNSATURATED AMIDES [J].

BOHLMANN, F ;

GANZER, M ;

KRUGER, M ;

NORDHOFF, E .

TETRAHEDRON, 1983, 39 (01) :123-128

[4]

BOHLMANN F, 1967, CHEM BER, P3861

[5] Cycloaddition of nitrile oxides to cyclic and acyclic α,β-unsaturated amides.: Frontier orbital interactions and an unexpected steric drift determine regiochemistry [J].

Caramella, P ;

Reami, D ;

Falzoni, M ;

Quadrelli, P .

TETRAHEDRON, 1999, 55 (22) :7027-7044

[6]

CARDILLO G, 1990, J CHEM SOC P1, P1587

[7] STUDIES ON THE BIOSYNTHESIS OF THE ANTIBIOTIC REDUCTIOMYCIN IN STREPTOMYCES-XANTHOCHROMOGENUS [J].

CHO, H ;

BEALE, JM ;

GRAFF, C ;

MOCEK, U ;

NAKAGAWA, A ;

OMURA, S ;

FLOSS, HG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) :12296-12304

[8]

Concellon J.M., 2000, ANGEW CHEM, V112, P2866

[9] Unusual reductive cleavage of 3-aryl-2,3-epoxyamides by using samarium diiodide.: Synthesis of 3-aryl-3-deuterio-2-hydroxyamides with total regioselectivity [J].

Concellón, JM ;

Bardales, E ;

Gómez, C .

TETRAHEDRON LETTERS, 2003, 44 (28) :5323-5326

[10] Transformation of α,β-epoxyesters into 2,3-dideuterioesters promoted by samarium diiodide [J].

Concellón, JM ;

Bardales, E ;

Llavona, R .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1585-1588

← 1 2 3 4 5 →