Organic Chemistry

A Highly Stereoselective Claisen-Sakurai Approach to Densely Functionalized Cyclopentenols



The formation of highly substitiuted cyclopentenols was developed using a Claisen-Sakurai reaction. Both elements of the reaction can be performed in a one-pot sequence that provides the corresponding cyclized products in high stereoselectivity. The stereochemical outcome is defined by a combination of Claisen stereospecificity and stereoelectronic effects in the Sakurai cyclization that promotes reactivity via a syn-SE’ antiperiplanar transition-state. This was determined by examination of the product stereochemistry and through detailed DFT analysis.


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