Abstract
3-Methyl-2,3-diphenyl-and 3-methyl-2-phenylcyclopropenones react with NaCN and water or alcohols as nucleophiles in the presence of NaHSO4 to give novel compounds, namely, 3-cyano-2,3-diphenylpropionic acid or alkyl 3-cyano-2,3-diphenyl-and alkyl 3-cyano-2-methyl-3-phenylpropionates. A reaction mechanism was proposed. The anti-(R*R*)-diastereomer was found to be the major reaction product.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2066–2069, September, 2005.
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Skornyakov, Y.V., Tereshchenko, D.S., Ignatenko, A.V. et al. A new example of the three-component reaction: nucleophilic ring opening in cyclopropenones by cyanide ions in the presence of water or alcohols. Russ Chem Bull 54, 2129–2132 (2005). https://doi.org/10.1007/s11172-006-0087-4
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DOI: https://doi.org/10.1007/s11172-006-0087-4