Oxidative Cyclization of Diols Derived from 1,5‐Dienes: Formation of Enantiopure  cis ‐Tetrahydrofurans by Using Catalytic Osmium Tetroxide; Formal Synthesis of (+)‐ cis ‐Solamin | Zendy

Donohoe Timothy J. | Zendy; Butterworth Sam | Zendy

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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.

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