Deconjugative conversion of alpha-alkynyl esters to alpha,alpha-disubstituted beta-alkynyl esters |
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Authors: | Lepore Salvatore D He Yuanjun |
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Institution: | Department of Chemistry, Florida Atlantic University, Boca Raton, FL 33431-0991, USA. slepore@fau.edu |
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Abstract: | We report the development of a method for the conversion of a variety of conjugated alpha-alkynyl esters to alpha,alpha-disubstituted beta-alkynylesters through the use of strong amide bases. Studies indicate that the second equivalent of base leads to the dianion intermediate. Optimal conditions included the use of 2 equiv of lithium diisopropylamide in THF with HMPA as the cosolvent followed by trapping with a variety of carbon electrophiles. Trapping with bis-electrophiles leads to spiro cycloalkane products. |
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