Chemoselective Syntheses of γ-Butyrolactams Using Vinyl Sulfilimines and Dichloroketene

Reactions between vinyl sulfilimines and dichloroketene generated in situ from trichloroacetyl chloride in the presence of zinc−copper couple give mixtures of α-dichloro-γ-butyrolactams and α-dichloro-γ-butyrolactone imines. Fine-tuning of substituents within vinyl sulfilimines results in reactions...

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Veröffentlicht in:	Organic letters 2005-05, Vol.7 (10), p.1915-1917
Hauptverfasser:	Marino, Joseph P, Zou, Nanfei
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Dichloroethylenes - chemistry Imines - chemistry Lactams - analysis Lactams - chemical synthesis Lactams - chemistry Molecular Structure Stereoisomerism Sulfur Compounds - chemistry Vinyl Compounds - chemistry
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Beschreibung
Zusammenfassung:	Reactions between vinyl sulfilimines and dichloroketene generated in situ from trichloroacetyl chloride in the presence of zinc−copper couple give mixtures of α-dichloro-γ-butyrolactams and α-dichloro-γ-butyrolactone imines. Fine-tuning of substituents within vinyl sulfilimines results in reactions with good chemoselectivity and yield for lactams.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol050245m