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Note | Regular issue | Vol 45, No. 5, 1997, pp.943-948
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7685
Synthetic Route to α-Phosphono-γ-butyrolactones: Synthesis of γ-Substituted α-Methylene-γ-butyro-lactones

Chi-Wan Lee, Jun Mo Gil, and Dong Young Oh*

*Department of Chemistry, Korea Advanced Institute of Science and Technology, 373-1, Kusung-Dong, Yusung-Gu, Taejon, 305-701, Korea

Abstract

Treatment of lithiated homoallylic phosphonates wiht dimethyl carbamyl chloride gave 2-amidophosphonate derivatives. A solution of 2-amidophosphonate in DME-H2O (2:1 vol) reacted with 2 eq. iodine at room temperature to give α-phosphono-γ-iodoalkyl-γ-butyrolactones in good yield, although the products are mixture. Wadsworth-Emmons reaction of α-phosphono-γ-iodoalkyl-γ-butyrolactones with aldehydes gave α-(alkyl)methylene-γ-iodoalkyl-γ-butyrolactone derivatives.