Development of the Juliá asymmetric epoxidation reaction. Part 2. Application of the oxidation to alkyl enones, enediones and unsaturated keto esters

W Kroutil, ME Lasterra-Sánchez, SJ Maddrell…

Index: Kroutil, Wolfgang; Lasterra-Sanchez, M. Elena; Maddrell, Samuel J.; Mayon, Patrick; Morgan, Phillip; Roberts, Stanley M.; Thornton, Steven R.; Todd, Christine J.; Tueter, Melek Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 23 p. 2837 - 2844

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Citation Number: 43

Abstract

Polyleucine-based systems have been used to catalyse the asymmetric oxidation of a variety of alkyl enones 1–4, 9–14, an enynone 16 and a dienone 17 to afford the corresponding epoxides 5–8, 18–26 in good to excellent yield and optical purity. A range of enediones 30–32, 34 and one unsaturated keto ester 33 have also been epoxidised stereoselectivley to afford optically active epoxides 35–39. The epoxidations were carried ...