Reaction of pyridine N-oxides with Grignard reagents:: a stereodefined synthesis of substituted dienal oximes

被引：25

作者：

Andersson, Hans

Wang, Xiaoyang

Bjorklund, Mikael

Olsson, Roger

Almqvist, Fredrik ^{[1
]}

机构：

[1] Umea Univ, Dept Chem, SE-90187 Umea, Sweden

[2] ACADIA Pharmaceut AB, S-20512 Malmo, Sweden

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 39期

关键词：

D O I：

10.1016/j.tetlet.2007.07.161

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rapid addition of Grignard reagents to pyridine N-oxides under mild conditions gave stereodefined dienal oximes in good to excellent yields. This reaction provides an efficient access to substituted olefins with defined stereochemistry that are potentially of interest as bioactives themselves or as versatile synthetic intermediates. (C) 2007 Elsevier Ltd. All rights reserved.

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页码：6941 / 6944

页数：4

相关论文

共 32 条

[1] Synthesis of 2-substituted pyridines via a regiospecific alkylation, alkynylation, and arylation of pyridine N-oxides [J].

Andersson, Hans ;

Almqvist, Fredrik ;

Olsson, Roger .

ORGANIC LETTERS, 2007, 9 (07) :1335-1337

[2]

[Anonymous], 1970, CHEM CARBON NITROGEN

[3] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].

Campeau, LC ;

Rousseaux, S ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021

[4] A practical, efficient, and rapid method for the oxidation of electron deficient pyridines using trifluoroacetic anhydride and hydrogen peroxide-urea complex [J].

Caron, S ;

Do, NM ;

Sieser, JE .

TETRAHEDRON LETTERS, 2000, 41 (14) :2299-2302

[5] Practical and highly regio- and stereoselective synthesis of 2-substituted dihydropyridines and piperidines: Application to the synthesis of (-)-coniine [J].

Charette, AB ;

Grenon, M ;

Lemire, A ;

Pourashraf, M ;

Martel, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (47) :11829-11830

[6] A simple and efficient method for the preparation of pyridine N-oxides [J].

Copéret, C ;

Adolfsson, H ;

Khuong, TAV ;

Yudin, AK ;

Sharpless, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05) :1740-1741

[7] Palladium catalyzed activation of borane-amine adducts:: rate enhancement of amine-borane methanolysis in the reduction of nitrobenzenes to anilines [J].

Couturier, M ;

Tucker, JL ;

Andresen, BM ;

Dubé, E ;

Brenek, SJ ;

Negri, JT .

TETRAHEDRON LETTERS, 2001, 42 (12) :2285-2288

[8] The Michael reaction of enaminones with N-(p-tolyl)-maleimide:: Synthesis and structural analysis of succinimide-enaminones [J].

Cunha, S ;

Rodovalho, W ;

Azevedo, NR ;

Mendonça, MD ;

Lariucci, C ;

Vencato, I .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2002, 13 (05) :629-634

[9] REDUCTION OF OXIMES, OXIME ETHERS, AND OXIME ESTERS WITH DIBORANE - A NOVEL SYNTHESIS OF AMINES [J].

FEUER, H ;

BRAUNSTEIN, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (06) :1817-+

[10]

Gribble GW, 1998, CHEM SOC REV, V27, P395

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