Stereoselective N-heterocyclic-carbene-catalyzed spiroannulation as an access towards spirobenzofuranone-fused cyclohexenones

08 May 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Heterocyclic spirocyclic compounds as structurally unique compounds are present in many natural or bioactive compounds. Not surprisingly, developing novel methodologies that enable stereocontrol access toward spirocyclic compounds represents an important goal in modern synthetic chemistry. The main interest is oriented toward developing methods for accessing spirooxindoles. On the other hand, the development of their oxygen-containing cousins is still overlooked. Here, we report a simple organocatalytic spiroannulation method, which provides access to spirocyclic benzofuran-2-ones. The utility of the protocol was underscored by gram-scale reaction and follow-up transformations.

Supplementary materials

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Supplementary Information
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Reaction conditions optimization, characterization data, crystallographic data, copies of 1H NMR, 13C NMR, 19F NMR, and chiral HPLC
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