Application of 1-tert-butoxy-3-[(trimethylsilyl) oxy] buta-1, 3-diene in the preparation of functionalized. beta.-hydroxycyclohexanone derivatives, including valuable …

RP Potman, N Janssen, JW Scheeren…

Index: Potman; Janssen; Scheeren; Nivard Journal of Organic Chemistry, 1984 , vol. 49, # 19 p. 3628 - 3634

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Citation Number: 18

Abstract

The usefulness of l-tert-butoxy-3-[(trimethylsilyl) oxy] buta-1, 3-diene asa valuable precursor for the synthesis of 3-hydroxycyclohexanone derivatives has been demonstrated. With a variety of electron-poor alkenes high yields of Diels-Alder adducts were obtained which were transformed into 3-tert-butoxycyclohexanones by mild acid hydrolysis. After protection of the keto group by acetalization with ethylene glycol the tert-butoxy group was converted ...