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

Wolfgang Kroutil*, M. Elena Lasterra-Sánchez, Samuel J. Maddrell, Patrick Mayon, Phillip Morgan, Stanley M. Roberts, Steven R. Thornton, Christine J. Todd, Melek Tüter

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47 Atıf (Scopus)

Özet

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 stereoselectively to afford optically active epoxides 35-39. The epoxidations were carried out with basic peroxide as the oxidant; the polyleucine catalyst was prepared from leucine N-carboxyanhydride using 1,3-diaminopropane, water (employing a humidity cabinet) or a polystyrene immobilised amine as the initiator. Preliminary mass spectral data on material derived from L-leucine and 1,3-diaminopropane (DAP-PLL) suggest that the catalyst consists of material that contains 22 ± 10 leucine residues.

Orijinal dilİngilizce
Sayfa (başlangıç-bitiş)2837-2844
Sayfa sayısı8
DergiJournal of the Chemical Society, Perkin Transactions 1
Basın numarası23
DOI'lar
Yayın durumuYayınlandı - 7 Ara 1996
Harici olarak yayınlandıEvet

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