A General Approach to Aza-Heterocycles by Means of Domino Sequences Driven by Hydroformylation

被引：37

作者：

Airiau, Etienne ^{[1
]}

Spangenberg, Thomas ^{[1
]}

Girard, Nicolas ^{[1
]}

Schoenfelder, Angele ^{[1
]}

Salvadori, Jessica ^{[2
]}

Taddei, Maurizio ^{[2
]}

Mann, Andre ^{[1
]}

机构：

[1] Univ Strasbourg 1, Fac Pharm, Lab Pharmacochim Commun Cellulaire, LCI,UMR 7175, F-67401 Illkirch Graffenstaden, France

[2] Univ Siena, Dipartimento Farmaco Chim Tecnol, I-53100 Siena, Italy

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 35期

关键词：

cyclohydrocarbonylation; diastereoselectivity; domino reactions; heterocycles; hydroformylation;

D O I：

10.1002/chem.200801795

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of hydroformylative domino reactions of easily accessible vinyl acetamides is described. Extremely regioselective hydroformylation of terminal double bounds provides a transient N-acyliminium that can be trapped by various nucleophiles to give several aza-heterocylic scaffolds in a diastereoselective manner.

引用

收藏

页码：10938 / 10948

页数：11

相关论文

共 38 条

[1] Facile and highly stereoselective synthesis of the tetracyclic erythrinane core [J].

Allin, SM ;

James, SL ;

Elsegood, MRJ ;

William, PM .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26) :9464-9467

[2] Synthesis of enantiopure trans-3,4-disubstituted piperidines.: An enantiodivergent synthesis of (+)- and (-)-paroxetine [J].

Amat, M ;

Bosch, J ;

Hidalgo, J ;

Cantó, M ;

Pérez, M ;

Llor, N ;

Molins, E ;

Miravitlles, C ;

Orozco, M ;

Luque, J .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3074-3084

[3] Cascade iminium ion reactions for the facile synthesis of quinolizidines.: Concise syntheses of (±)-epilupinine and (-)-epimyrtine [J].

Amorde, SM ;

Judd, AS ;

Martin, SF .

ORGANIC LETTERS, 2005, 7 (10) :2031-2033

[4]

[Anonymous], 2000, ORGANIC REACTIONS

[5] High yields of diazabicycloalkanes and oxazabicycloalkanes containing medium and large rings from rhodium-catalysed hydroformylation reactions without the need for high dilution conditions [J].

Bergmann, DJ ;

Campi, EM ;

Jackson, WR ;

Patti, AF .

CHEMICAL COMMUNICATIONS, 1999, (14) :1279-1280

[6]

Billig E., 1988, U.S. Patent, Patent No. [4,668,651, 4668651]

[7] Hydrogen bonding as a construction element for bidentate donor ligands in homogeneous catalysis: Regioselective hydroformylation of terminal alkenes [J].

Breit, B ;

Seiche, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6608-6609

[8]

Breit B, 2001, SYNTHESIS-STUTTGART, P1

[9] Rhodium-catalyzed cyclohydrocarbonylation approach to the syntheses of enantiopure homokainoids [J].

Chiou, Wen-Hua ;

Schoenfelder, Angele ;

Sun, Liang ;

Mann, Andre ;

Ojima, Iwao .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25) :9418-9425

[10] Highly efficient synthesis of azabicyclo[x.y.0]alkane amino acids and congeners by means of Rh-catalyzed cyclohydrocarbonylation [J].

Chiou, Wen-Hua ;

Mizutani, Nobihiro ;

Ojima, Iwao .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (06) :1871-1882

← 1 2 3 4 →