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Paper | Regular issue | Vol 36, No. 4, 1993, pp.799-817
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6239
Ring-Opening of Isoxazolidine Nucleus by Trimethyl Posphate Treatment: Formation of Tertiary Allylic Alcohols via Intermediate 1,3-Oxazinium Salts

Ugo Chiacchio, Angelo Liguori, Giovanni Romeo,* Giovanni Sindona, and Nicola Uccella*

*Dipartimento Farmaco-Chimico, Università di Messina, Viale Annunziata, 98168 Messina, Italy


5,5-Disubstituted Isoxazolidines undergo ring opening reaction, leading to tertiary allylic alcohols, by sequential treatment with trimethyl phosphate (TMP) and NaH. The reaction proceeds through sequence steps which involve an initial alkylation to isoxazolidinium intermediate, followed by ring expansion to tetrahydro-1,3-oxazine, further alkylation and a Hofmann-like elimination towards the final products promoted by NaH.