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Methyltrioxorhenium‐Catalyzed Epoxidation‐Methanolysis of Glycals under Homogeneous and Heterogeneous Conditions
Author(s) -
Goti Andrea,
Cardona Francesca,
Soldaini Gianluca,
Crestini Claudia,
Fiani Cinzia,
Saladino Raffaele
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505412
Subject(s) - chemistry , catalysis , homogeneous , amine gas treating , substrate (aquarium) , polystyrene , organic chemistry , homogeneous catalysis , heterogeneous catalysis , combinatorial chemistry , polymer , physics , oceanography , thermodynamics , geology
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.