Preparation of enol ester epoxides and their ring-opening to [alpha]-silyloxyaldehydes

The Z-selective ruthenium-catalyzed addition of aromatic carboxylic acids to alkynes was followed by dioxirane epoxidation to furnish enol ester epoxides with cis configuration. Upon treatment of enol ester epoxides with tert-butyldimethylsilyl triflate in the presence of 2,6-lutidine, synthetically...

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Veröffentlicht in:	Tetrahedron letters 2012-09, Vol.53 (38), p.5064-5067
Hauptverfasser:	Friestad, Gregory K, Sreenilayam, Gopeekrishnan, Cannistra, Joseph C, Slominski, Luke M
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkynes Carboxylic acids Dioxirane Epoxidation Esters Microwaves Tetrahedrons Transformations
Online-Zugang:	Volltext
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Beschreibung
Zusammenfassung:	The Z-selective ruthenium-catalyzed addition of aromatic carboxylic acids to alkynes was followed by dioxirane epoxidation to furnish enol ester epoxides with cis configuration. Upon treatment of enol ester epoxides with tert-butyldimethylsilyl triflate in the presence of 2,6-lutidine, synthetically useful [alpha]-silyloxyaldehydes were obtained. This novel transformation was facilitated by microwave irradiation.
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2012.06.142