Article ID Journal Published Year Pages File Type
5221676 Tetrahedron 2011 8 Pages PDF
Abstract

(Silyl)methylallenic amines were synthesized by the chromium-catalyzed addition of (4-bromobutynyl)trimethylsilane to tosyl imines. Regioisomeric mixtures of the desired allene and the corresponding alkyne were obtained. Allenic imines were then treated with TBAF to afford 2-aminomethyl-1,3-dienes in good yields (62-92%). In the presence of a Lewis acid, silylallenic imines were added to benzaldehyde dimethylacetal to give highly functionalized dienes with excellent yields and good to excellent diastereomeric ratios.

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Physical Sciences and Engineering Chemistry Organic Chemistry
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