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Methyltrioxorhenium-Catalyzed Epoxidation-Methanolysis of Glycals under Homogeneous and Heterogeneous Conditions

✍ Scribed by Andrea Goti; Francesca Cardona; Gianluca Soldaini; Claudia Crestini; Cinzia Fiani; Raffaele Saladino

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 163 KB
Volume: 348
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.200505412

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✦ Synopsis

Abstract

The efficient and high yielding domino epoxidation‐methanolysis of glycals 8–15 has been achieved by oxidation with UHP in MeOH catalyzed by MTO. The products have been conveniently isolated as 2‐acetoxy derivatives 16–23a, b by direct acetylation of the crude mixtures. Homogeneous MTO‐amine complexes 5–7, heterogeneous poly(4‐vinylpyridine)/MTO compounds I–III, and microencapsulated polystyrene/MTO systems IV–VII were also tested and demonstrated their effectiveness as catalysts for the oxidation step. The facial diastereoselectivity of the oxidation ranged from satisfactory to excellent depending on the substrate and could be optimized by ample screening of catalysts. Complete conversions of substrates and nearly quantitative yields of products were obtained under environmentally friendly experimental conditions and with the use of simple work‐up procedures.

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