Synthesis of 2-amino-1,3-dienes by chromium-catalyzed addition of silylated propargyl bromides to imines |
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Authors: | Marí a Durá n-Galvá nBrian T. Connell |
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Affiliation: | Department of Chemistry, Texas A&M University, PO Box 30012, College Station, TX 77842-3012, USA |
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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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Keywords: | Chromium Dienes Allenes Imines Regioselectivity |
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