Short Access to (+)-Lupinine and (+)-Epiquinamide via Double Hydroformylation

被引：60

作者：

Airiau, Etienne ^{[2
]}

Spangenberg, Thomas ^{[1
,2
]}

Girard, Nicolas ^{[2
]}

Breit, Bernhard ^{[1
]}

Mann, Andre ^{[2
]}

机构：

[1] Univ Freiburg, Inst Organ Chem & Biochem, D-79104 Freiburg, Germany

[2] Univ Strasbourg, Fac Pharm, CNRS, Lab Innovat Therapeut,UMR 7200, F-67401 Illkirch Graffenstaden, France

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 03期

关键词：

STEREOSELECTIVE ALDOL REACTIONS; ENANTIOSELECTIVE SYNTHESIS; CATALYZED CYCLOHYDROCARBONYLATION; ALLYLBORATION-HYDROFORMYLATION; SYNTHETIC APPLICATIONS; ASYMMETRIC SYNTHESES; ATOM ECONOMY; METATHESIS; INDOLIZIDINE; EPIQUINAMIDE;

D O I：

10.1021/ol902718q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Short and efficient access to (+)-lupinine and (+)-epiquinamide by means of an unprecedented double hydroformylation of a bis-homoallylic azide followed by a tandem catalytic hydrogenation/reductive bis-amination is reported.

引用

页码：528 / 531

页数：4

共 62 条

[1] Glycosidic alkaloids from Lupinus varius [J].

Abdel-Halim, OB ;

El-Gammal, AA ;

Abdel-Fattah, H ;

Takeya, K .

PHYTOCHEMISTRY, 1999, 51 (01) :5-9

[2] L-VINYLGLYCINE [J].

AFZALIARDAKANI, A ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (24) :4817-4820

[3] Enantioselective synthesis of indolizidine and quinolizidine derivatives from chiral non-racemic bicyclic lactams [J].

Agami, C ;

Dechoux, L ;

Hebbe, S ;

Ménard, C .

TETRAHEDRON, 2004, 60 (25) :5433-5438

[4] Four-Component Reactions toward Fused Heterocyclic Rings [J].

Airiau, Etienne ;

Girard, Nicolas ;

Mann, Andre ;

Salvadori, Jessica ;

Taddei, Maurizio .

ORGANIC LETTERS, 2009, 11 (22) :5314-5317

[5] A General Approach to Aza-Heterocycles by Means of Domino Sequences Driven by Hydroformylation [J].

Airiau, Etienne ;

Spangenberg, Thomas ;

Girard, Nicolas ;

Schoenfelder, Angele ;

Salvadori, Jessica ;

Taddei, Maurizio ;

Mann, Andre .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (35) :10938-10948

[6] Convenient asymmetric syntheses of anti-beta-amino alcohols [J].

Barrett, AGM ;

Seefeld, MA ;

White, AJP ;

Williams, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) :2677-2685

[7]

Billig E., 1987, US Patent, Patent No. 4668651

[8]

Billig E., 1988, US Patent, Patent No. [4,769,498, 4769498]

[9] ASYMMETRIC ALDOL REACTIONS - A NEW CAMPHOR-DERIVED CHIRAL AUXILIARY GIVING HIGHLY STEREOSELECTIVE ALDOL REACTIONS OF BOTH LITHIUM AND TITANIUM(IV) ENOLATES [J].

BONNER, MP ;

THORNTON, ER .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) :1299-1308

[10] Organic azides:: An exploding diversity of a unique class of compounds [J].

Bräse, S ;

Gil, C ;

Knepper, K ;

Zimmermann, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240

← 1 2 3 4 5 6 7 →