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Oxidative Cyclization of Diols Derived from 1,5‐Dienes: Formation of Enantiopure cis ‐Tetrahydrofurans by Using Catalytic Osmium Tetroxide; Formal Synthesis of (+)‐ cis ‐Solamin
Author(s) -
Donohoe Timothy J.,
Butterworth Sam
Publication year - 2005
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.200500513
Subject(s) - enantiopure drug , osmium tetroxide , formal synthesis , chemistry , trifluoroacetic acid , catalysis , vicinal , osmium , enantiomer , natural product , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , ruthenium , physics , electron microscope , optics
High yields and high levels of stereocontrol are observed in the oxidative cyclization of vicinal diols using catalytic amounts of a transition metal (see scheme; TFA=trifluoroacetic acid). The product stereochemistry is controlled completely by the starting material, and, importantly, single enantiomers can be accessed readily. The reaction sequence is demonstrated in a very short formal synthesis of the natural product (+)‐ cis ‐solamin.