The stereoselective synthesis of oxetanes; exploration of a new, Mitsunobu-style procedure for the cyclisation of 1, 3-diols

M Christlieb, JE Davies, J Eames, R Hooley…

Index: Christlieb; Davies; Eames; Hooley; Warren Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 22 p. 2983 - 2996

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Citation Number: 20

Abstract

A solution of 2-methyl-3-[1-(phenylsulfanyl) cyclohexyl] propane-1, 3-diol 1 in toluene treated with triphenylphosphine, Ziram® 2 and DEAD, gave 3-methyl-2-[1-(phenylsulfanyl) cyclohexyl] oxetane 3 in 85% yield. A mechanistic study has been undertaken, optimal conditions have been found and the range of substrates for which the reaction is useful has been explored. We include the results of an X-ray study which shows that compound 33 ( ...

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