Anodic Cyclization Reactions: Reversing the Polarity of Ketene Dithioacetal Groups

Intramolecular coupling reactions of ketene dithioacetal groups with enol ether and alcohol nucleophiles have been studied. The reactions were initiated by an anodic oxidation of the ketene dithioacetal and proved to be compatible with the formation of five- or six-member rings, as well as the stere...

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Veröffentlicht in:	Organic letters 2001-05, Vol.3 (11), p.1729-1732
Hauptverfasser:	Sun, Yongmao, Liu, Bin, Kao, Jeff, d'Avigno, D. Andre', Moeller, Kevin D
Format:	Artikel
Sprache:	eng
Schlagworte:	Cyclization Ketones - chemical synthesis Oxidation-Reduction Stereoisomerism Thioacetamide - analogs & derivatives Thioacetamide - chemical synthesis
Online-Zugang:	Volltext
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Beschreibung
Zusammenfassung:	Intramolecular coupling reactions of ketene dithioacetal groups with enol ether and alcohol nucleophiles have been studied. The reactions were initiated by an anodic oxidation of the ketene dithioacetal and proved to be compatible with the formation of five- or six-member rings, as well as the stereoselective generation of quaternary carbons.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol015925d