Synthesis of CF-containing spiro-epoxyoxindoles via the Corey-Chaykovsky reaction of N-alkyl isatins with PhSCHCFOTf.

Org Biomol Chem

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.

Published: May 2018

CF3-containing spiro-epoxyoxindoles were successfully prepared via the Corey-Chaykovsky reaction of N-alkyl isatins with the ylide generated from Ph2S+CH2CF3OTf- with almost exclusive diastereoselectivity. Further derivatizations of these spiro-epoxyoxindoles were explored via a photochemical reaction or Lewis acid-promoted allylation.

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http://dx.doi.org/10.1039/c8ob00602dDOI Listing

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