Unexpected Ring-Opening Reactions of Aziridines with Aldehydes Catalyzed by Nucleophilic Carbenes under Aerobic Conditions

Unexpected Ring-Opening Reactions of Aziridines with Aldehydes Catalyzed by Nucleophilic Carbenes under Aerobic Conditions

The chemoselective ring opening of N-tosyl aziridines with aldehydes catalyzed by an N-heterocyclic carbene was investigated under aerobic conditions. Unexpected carboxylates of 1,2-amino alcohols from the corresponding aldehydes, rather than the acyl anion ring-opened β-amino ketones, were exclusiv...

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Veröffentlicht in:Organic letters 2006-04, Vol.8 (8), p.1521-1524
Hauptverfasser: Liu, Yan-Kai, Li, Rui, Yue, Lei, Li, Bang-Jing, Chen, Ying-Chun, Wu, Yong, Ding, Li-Sheng
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Aziridines - chemistry
Catalysis
Hydrocarbons - chemistry
Methane - analogs & derivatives
Methane - chemistry
Models, Molecular
Molecular Structure
Oxidation-Reduction
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Zusammenfassung:The chemoselective ring opening of N-tosyl aziridines with aldehydes catalyzed by an N-heterocyclic carbene was investigated under aerobic conditions. Unexpected carboxylates of 1,2-amino alcohols from the corresponding aldehydes, rather than the acyl anion ring-opened β-amino ketones, were exclusively obtained. A plausible mechanism for this unprecedented carbene-mediated reaction was also proposed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0529905