One-Pot,Fluoride-Promoted Wittig Reaction |
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Authors: | Tiziano Fumagalli Guido Sello |
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Institution: | Department of Organic and Industrial Chemistry , University of Milan , Milan, Italy |
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Abstract: | A one-pot, fluoride-promoted Wittig reaction was developed. The reactions of ethyl α-bromoacetate with aliphatic, aromatic, and heteroaromatic aldehydes in the presence of tri-n-butylphosphine and tetrabutylammonium fluoride produced α,β-unsaturated esters in good to excellent yields and E-stereoselectivity. Under the same conditions, reactions of ethyl α-bromopropionate, α-bromo acetonitrile, and α-bromoacetophenone with aliphatic and aromatic aldehydes in the presence of tri-n-butylphosphine and tetrabutylammonium fluoride produced the expected α,β-unsaturated derivatives in good E-stereoselectivity. The protocol was extended to semistabilized ylides and applied to the synthesis of some combretastatin analogs. |
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Keywords: | Tetra-n-butylammonium fluoride α" target="_blank">α β-unsaturated compounds" target="_blank">β-unsaturated compounds Wittig reaction |
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