One-pot enol silane formation-Mukaiyama aldol-type addition to dimethyl acetals mediated by TMSOTf.
نویسندگان
چکیده
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.
منابع مشابه
A Tandem Enol Silane Formation-Mukaiyama Aldol Reaction Mediated by TMSOTf
A slight excess of silyl trifluoromethanesulfonate mediates a tandem enol silane formation-Mukaiyama aldol reaction in the presence of Hunig’s base. Preformation of the enol silane is unnecessary for efficient reactions, which proceed in 75-97% yield for the addition of aryl methyl ketones and acetate esters to non-enolizable aldehydes. Mechanistic data suggests that free amine is crucial for f...
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عنوان ژورنال:
- The Journal of organic chemistry
دوره 73 8 شماره
صفحات -
تاریخ انتشار 2008