Inverse electron-demand aza-[4+2] cycloaddition reactions of allenamides

被引：45

作者：

Berry, CR ^{[1
]}

Hsung, RP ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

TETRAHEDRON | 2004年 / 60卷 / 35期

基金：

美国国家科学基金会;

关键词：

allenamides; Diels-Alder; cycloaddition; inverse demand; l-azadiene; aza-glycoside;

D O I：

10.1016/j.tet.2004.05.117

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An inverse electron-demand aza-[4+2] cycloaddition reaction of allenamides with 1-azadiene is described here. Effects of solvents on diastereoselectivity along with synthetic scopes and mechanistic insights are illustrated. Despite some synthetic limitations, this aza-[4+2] cycloaddition does provide a useful template for the synthesis of aza-glycoside related heterocycles. (C) 2004 Elsevier Ltd. All rights reserved.

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收藏

页码：7629 / 7636

页数：8

相关论文

共 102 条

[1] Asymmetric synthesis of 2-amino-3-hydroxynorbornene-2-carboxylic acid derivatives [J].

Abbiati, G ;

Clerici, F ;

Gelmi, ML ;

Gambini, A ;

Pilati, T .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6299-6304

[2] Synthesis of 1-deoxy-D-galactohomonojirimycin via enantiomerically pure allenylstannanes [J].

Achmatowicz, M ;

Hegedus, LS .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2229-2234

[3] EPOXIDATION OF VINYLAMIDES BY DIMETHYLDIOXIRANE - FIRST SPECTRAL EVIDENCE FOR ENAMIDE OXIDES [J].

ADAM, W ;

REINHARDT, D ;

REISSIG, HU ;

PAULINI, K .

TETRAHEDRON, 1995, 51 (45) :12257-12262

[4]

[Anonymous], 1989, PROG HET CH

[5] Facial diastereoselectivity in the photocycloaddition of chiral N-acyl enamines to benzaldehyde [J].

Bach, T ;

Schröder, J ;

Brandl, T ;

Hecht, J ;

Harms, K .

TETRAHEDRON, 1998, 54 (18) :4507-4520

[6]

BALASUBRAMANIAN KK, 1974, TETRAHEDRON LETT, P2643

[7] Diels-Alder reactions of N-silyloxy 1-azadienes [J].

Behforouz, M ;

Gu, ZX ;

Stelzer, LS ;

Ahmadian, M ;

Haddad, J ;

Scherschel, JA .

TETRAHEDRON LETTERS, 1997, 38 (13) :2211-2214

[8] A HIGHLY CONCISE SYNTHESIS OF LAVENDAMYCIN METHYL-ESTER [J].

BEHFOROUZ, M ;

GU, ZX ;

CAI, W ;

HORN, MA ;

AHMADIAN, M .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :7089-7091

[9]

Berry CR, 2003, SYNLETT, P791

[10] Total synthesis of (+)-camptothecin [J].

Blagg, BSJ ;

Boger, DL .

TETRAHEDRON, 2002, 58 (32) :6343-6349

← 1 2 3 4 5 6 7 8 9 10 →