I. Lewis Base-promoted Additions of Trialkoxysilylalkynes. II. Multicomponent Homoenolate Reactions Using Acylsilanes

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Northwestern University, 2007 - 237 pages
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Lewis base-catalyzed activation of triethoxysilylalkynes promotes the addition of alkynyl units to aldehydes and ketones. The resulting propargyl alcohols are isolated in high yields. The use of Lewis base catalysis in this reaction allows for the mild acetylide generation. This facet allows for the addition of alkynyl units to base-sensitive functionality (e.g. aliphatic aldehydes and ketones) and for the selective addition to aldehydes and ketones in the presence of other carbonyl functionality (e.g. esters). Mechanistic studies indicate that the reaction is proceeding by an auto-catalytic cycle. Additionally, the Lewis base-activated pentavalent intermediate can be visualized by low temperature 29Si NMR spectroscopy. Furthermore, the developed reaction has been applied to the diastereoselective Lewis base-promoted addition of alkynes to N-tert-butanesulfonyl imines, affording chiral propargyl amines in exceptional yield and selectivity.

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