Nonstabilized Azomethine Ylides in the Mannich Reaction: Synthesis of 3,3-Disubstituted Pyrrolidines, Including Oxindole Alkaloids

被引：31

作者：

Buev, Evgeny M. ^{[1
]}

Moshkin, Vladimir S. ^{[1
]}

Sosnovskikh, Vyacheslav Y. ^{[1
]}

机构：

[1] Ural Fed Univ, Inst Nat Sci & Math, Ekaterinburg 620000, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 23期

基金：

俄罗斯科学基金会;

关键词：

ALPHA-AMINO-ACIDS; C-H FUNCTIONALIZATION; ONE-POT SYNTHESIS; DECARBOXYLATIVE ROUTE; AROMATIC-ALDEHYDES; 5-ARYLOXAZOLIDINES; CYCLOADDITIONS; (+/-)-COERULESCINE; (-)-HORSFILINE; INTERMEDIATE;

D O I：

10.1021/acs.joc.7b02193

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Active methylene compounds react with in situ generated nonstabilized azomethine ylides via the domino Mannich reaction-dipolar cycloaddition to form 3,3-disubstituted pyrrolidines, including oxindole alkaloids. When the starting material possesses a single activated hydrogen, the reaction terminates at the Mannich base stage. The developed methodology was applied to a short and efficient synthesis of (+/-)-horsfiline and N-protected (+/-)-coerulescine.

引用

页码：12827 / 12833

页数：7

共 48 条

[1] Electrocyclization reactions of vinyl, styryl, and butadienyl conjugated carbonyl/azomethine ylides [J].

Anac, Olcay ;

Gungor, Fusun Seyma .

TETRAHEDRON, 2010, 66 (32) :5931-5953

[2] The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids [J].

Bi, Hai-Peng ;

Zhao, Liang ;

Liang, Yong-Min ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) :792-795

[3] Spiroanthraceneoxazolidine as a synthetic equivalent of methanimine in the reaction with donor-acceptor cyclopropanes. Synthesis of diethyl 5-arylpyrrolidine-3,3-dicarboxylates [J].

Buev, Evgeny M. ;

Moshkin, Vladimir S. ;

Sosnovskikh, Vyacheslav Y. .

TETRAHEDRON LETTERS, 2016, 57 (33) :3731-3734

[4] Reagents for Storage and Regeneration of Nonstabilized Azomethine Ylides: Spiroanthraceneoxazolidines [J].

Buev, Evgeny M. ;

Moshkin, Vladimir S. ;

Sosnovskikh, Vyacheslav Y. .

ORGANIC LETTERS, 2016, 18 (08) :1764-1767

[5] Synthesis of (alkylaminomethyl)lactones and hydroxypiperidones using alkylaminomethylation methodology [J].

Buev, Evgeny M. ;

Moshkin, Vladimir S. ;

Sosnovskikh, Vyacheslav Y. .

TETRAHEDRON LETTERS, 2015, 56 (47) :6590-6592

[6] Synthesis of spiropyrrolidines and spiropyrrolizidines by 1,3-dipolar cycloadditions of azomethine ylides to substituted α-methylene-γ-lactones [J].

Castulík, J ;

Marek, J ;

Mazal, C .

TETRAHEDRON, 2001, 57 (39) :8339-8347

[7] New Regio- and Stereoselective Cascades via Unstabilized Azomethine Ylide Cycloadditions for the Synthesis of Highly Substituted Tropane and Indolizidine Frameworks [J].

Chen, Shuming ;

Bacauanu, Vlad ;

Knecht, Tobias ;

Mercado, Brandon Q. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (38) :12664-12670

[8] Redox-Neutral α-Arylation of Amines [J].

Chen, Weijie ;

Wilde, Richard G. ;

Seidel, Daniel .

ORGANIC LETTERS, 2014, 16 (03) :730-732

[9] Intramolecular dipolar cycloaddition reactions of azomethine ylides [J].

Coldham, I ;

Hufton, R .

CHEMICAL REVIEWS, 2005, 105 (07) :2765-2809

[10] 1,3-Dipolar Cycloaddition-Decarboxylation Reactions of an Azomethine Ylide with Isatoic Anhydrides: Formation of Novel Benzodiazepinones [J].

D'Souza, Asha M. ;

Spiccia, Nadia ;

Basutto, Jose ;

Jokisz, Pawel ;

Wong, Leon S. -M. ;

Meyer, Adam G. ;

Holmes, Andrew B. ;

White, Jonathan M. ;

Ryan, John H. .

ORGANIC LETTERS, 2011, 13 (03) :486-489

← 1 2 3 4 5 →