A general approach to aza-heterocycles by means of domino sequences driven by hydroformylation

Etienne Airiau; Thomas Spangenberg; Nicolas Girard; Angèle Schoenfelder; Jessica Salvadori; Maurizio Taddei; André Mann

doi:10.1002/chem.200801795

A general approach to aza-heterocycles by means of domino sequences driven by hydroformylation

Chemistry. 2008;14(35):10938-48. doi: 10.1002/chem.200801795.

Authors

Etienne Airiau¹, Thomas Spangenberg, Nicolas Girard, Angèle Schoenfelder, Jessica Salvadori, Maurizio Taddei, André Mann

Affiliation

¹ Faculté de Pharmacie, Université Louis Pasteur de Strasbourg, Laboratoire de Pharmacochimie de la Communication Cellulaire UMR 7175/LC1, 74, route du Rhin, BP 60024, 67401 Illkirch, France.

PMID: 19009576
DOI: 10.1002/chem.200801795

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetamides / chemistry
Aza Compounds / chemical synthesis*
Cyclization
Formates
Heterocyclic Compounds / chemical synthesis*
Indicators and Reagents
Indolizines / chemical synthesis
Stereoisomerism

Substances

Acetamides
Aza Compounds
Formates
Heterocyclic Compounds
Indicators and Reagents
Indolizines
formic acid