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A General Oxidative Cyclization of 1,5‐Dienes Using Catalytic Osmium Tetroxide
Author(s) -
Donohoe Timothy J.,
Butterworth Sam
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200390253
Subject(s) - dihydroxylation , osmium tetroxide , diastereomer , stereoselectivity , chemistry , oxidative phosphorylation , osmium , catalysis , organic chemistry , combinatorial chemistry , enantioselective synthesis , biochemistry , ruthenium , physics , electron microscope , optics
Dihydroxylation of 1,5‐dienes under acidic conditions is sufficient to induce an efficient oxidative cyclization that produces stereochemically defined tetrahydrofurans in one step [Eq. (1)]. This method is very general and efficient for a range of dienes and shows complete stereoselectivity for formation of the 2,5‐ cis diastereoisomers. Bn=benzyl, CSA=camphorsulfonic acid.