Metal-catalyzed asymmetric 1,4-conjugate addition of vinylboron compounds to 2-substituted-4-oxy-cyclopent-2-en-1-ones yielding prostaglandins and prostaglandin analogs

This invention provides a novel method for the preparation of 2,3- disubstituted-4-oxy-cyclopentan-l-one compounds that are useful for the synthesis of prostaglandins and prostaglandin analogs of industrial relevance. The method comprises the metal -catalyzed asymmetric 1,4-conjugate addition of vin...

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Bibliographic Details
Main Authors Henschke, Julian Paul, Wu, Ping-yu, Wen, Wen-hsien, Wu, Hsyueh-liang
Format Patent
LanguageEnglish
Published 01.08.2019
Subjects
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
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Summary:This invention provides a novel method for the preparation of 2,3- disubstituted-4-oxy-cyclopentan-l-one compounds that are useful for the synthesis of prostaglandins and prostaglandin analogs of industrial relevance. The method comprises the metal -catalyzed asymmetric 1,4-conjugate addition of vinylboron compounds to 2- substituted-4-oxy-cyclopent-2-en-l-ones. This method relies on the use of less toxic, easily- handled reagents, and can be performed under milder conditions than offered by some conventional methods, affording 2,3-disubstituted-4-oxy-cyclopentan-l-one compounds enantio- and diastereoselectively, which are precursors to the said prostaglandin and prostaglandin analogs, in high yield.
Bibliography:Application Number: AU20150287220