Abstract
trans-1-Alkoxy-2-(phenylethynyl)cyclopropanes undergo lithiation at the hydrogen atom in the α-position to the triple bond on treatment with BuLi in THF at–(65—70) °C. The resulting organolithium derivatives react with acetaldehyde, acetone, dimethyl disulfide, and methyl chloroformate giving the corresponding alcohols, sulfides, and esters with the yields up to 69% with complete retention of cyclopropane ring stereoconfiguration. The obtained methyl 3-alkoxy-2,2-dimethyl-1-(phenylethynyl)cyclopropanecarboxylates and the corre-sponding acid readily undergo ring opening with addition of water molecule or HCl.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 0862—0866, May, 2017.
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Gvozdev, V.D., Shavrin, K.N., Ageshina, A.A. et al. Stereoselective functionalization of 1-alkoxy-2-(phenylethynyl)cyclopropanes via lithiation and subsequent reactions with electrophilic reagents. Russ Chem Bull 66, 862–866 (2017). https://doi.org/10.1007/s11172-017-1819-3
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DOI: https://doi.org/10.1007/s11172-017-1819-3