One-Pot Enol Silane Formation-Mukaiyama Aldol-Type Addition to Dimethyl Acetals Mediated by TMSOTf

Various ketones, esters, amides, and thioesters add in high yield to dimethyl acetals in the presence of silyl trifluoromethanesulfonates and an amine base. Acetals derived from aryl, unsaturated, and aliphatic aldehydes are all effective substrates. The reaction proceeds in a single reaction flask,...

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Veröffentlicht in:	Journal of organic chemistry 2008-04, Vol.73 (8), p.3299-3302
Hauptverfasser:	Downey, C. Wade, Johnson, Miles W., Tracy, Kathryn J.
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetals - chemistry Acetophenones - chemistry Aldehydes - chemistry Aliphatic compounds Benzaldehydes - chemistry Chemistry Exact sciences and technology Magnetic Resonance Spectroscopy Mesylates - chemistry Molecular Structure Organic chemistry Preparations and properties Silanes - chemical synthesis Silanes - chemistry Trimethylsilyl Compounds - chemistry
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Beschreibung
Zusammenfassung:	Various ketones, esters, amides, and thioesters add in high yield to dimethyl acetals in the presence of silyl trifluoromethanesulfonates and an amine base. Acetals derived from aryl, unsaturated, and aliphatic aldehydes are all effective substrates. The reaction proceeds in a single reaction flask, with no purification of the intermediate enol silane necessary.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo8001084