Synthesis of aliphatic (E)-α,β-unsaturated amides with high diastereoselectivity from α,β-epoxyamides promoted by SmI2/HMPA

被引：22

作者：

Concellón, JM ^{[1
]}

Bardales, E ^{[1
]}

机构：

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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 07期

关键词：

amides; alpha; beta-epoxyamides; samarium; synthesis design;

D O I：

10.1002/ejoc.200300641

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of aliphatic (E)-alpha,beta-unsaturated amides 2, in which the C=C bond is di- or trisubstituted, is achieved by using samarium diiodide and HMPA. The starting compounds 1 were easily prepared by the reaction of the corresponding lithium or potassium enolates of alpha-chloroamides with aldehydes. A mechanism to explain this process is proposed. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

引用

页码：1523 / 1526

页数：4

共 30 条

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

BALDWIN, JE ;

DUPONT, WA .

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

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

BOHLMANN, F ;

GANZER, M ;

KRUGER, M ;

NORDHOFF, E .

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

[3]

BOHLMANN F, 1967, CHEM BER, P3861

[4] 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

[5] 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

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

Concellón, JM ;

Bardales, E .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9492-9495

[7] Synthesis of (E)-α,β-unsaturated esters with total or high diastereoselectivity from α,β-epoxyesters [J].

Concellón, JM ;

Bardales, E .

ORGANIC LETTERS, 2002, 4 (02) :189-191

[8]

Concellón JM, 1999, ANGEW CHEM INT EDIT, V38, P2384, DOI 10.1002/(SICI)1521-3773(19990816)38:16<2384::AID-ANIE2384>3.0.CO

[9]

2-3

[10]

Concellón JM, 2000, ANGEW CHEM INT EDIT, V39, P2773, DOI 10.1002/1521-3773(20000804)39:15<2773::AID-ANIE2773>3.0.CO

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