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

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.

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Bibliographic Details
Published in:Organic letters 2010-02, Vol.12 (3), p.528-531
Main Authors: Airiau, Etienne, Spangenberg, Thomas, Girard, Nicolas, Breit, Bernhard, Mann, André
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Amination
Azides - chemistry
Catalysis
Chemical Sciences
Hydrogenation
Molecular Structure
Organic chemistry
Quinolizines - chemical synthesis
Quinolizines - chemistry
Sparteine - analogs & derivatives
Sparteine - chemical synthesis
Sparteine - chemistry
Stereoisomerism
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Description
Summary: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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol902718q