The Journal of Organic Chemistry

Upper excited state reactions of thioketenes: di-tert-butylthioketene

S Singh, V Ramamurthy

Index: Singh, Sharat; Ramamurthy, V. Journal of Organic Chemistry, 1984 , vol. 49, # 2 p. 393 - 395

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Citation Number: 5

Abstract

21 hl Through the use of E ~ ( fod ) ~ catalysis? the silyloxy diene 1912 reacts with the appropriate aromatic aldehyde to give enol ethers 20a6 and 20b6 in nearly quantitative yield. Compound 20b was hydrolyzed to the 2,6-disubstituted tetrahydropyrone 216 with aqueous HC1-THF. Thus, the endo selectivity of the europium-induced pericyclic reac- tion5 provides a stereospecific entry to cis-2,6-disubstituted tetrahydropyrones. Alternative possibilities for taking ...