Stereoselective Synthesis of 1-Methyl-3',4',5',6'-tetrahydrospiro[indoline-3,2'-pyran]-2-one Derivatives via Prins Cyclization.

J Org Chem

Department of Chemistry and Center for Diagnostics and Therapeutics, Georgia State University, Atlanta, Georgia 30303, United States.

Published: June 2015

A novel spirocyclization has been developed for the construction of functionalized spirooxindole pyran via Lewis acid promoted Prins cyclization. The reaction proceeds through formation of a single diastereoisomer with high stereoselectivity. This approach can be used to construct biologically important substituted spirooxindole as well as fluorinated pyran scaffolds.

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http://dx.doi.org/10.1021/acs.joc.5b00249DOI Listing

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