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
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United States of America Patent
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Jun 6, 2017
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Jul 9, 2015
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Jul 10, 2014
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Abstract
This invention provides a novel method for the preparation of 2,3-disubstituted -4-oxy-cyclopentan1-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-1-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-1-one compounds enantio- and diastereoselectively, which are precursors to the said prostaglandin and prostaglandin analogs, in high yield.
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