Enolate addition to bicyclobutanes enables expedient access to 2-oxo-bicyclohexane scaffolds

29 August 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report the synthesis of 2-oxo-bicyclo[2.1.1]hexanes (2-oxo-BCHs) from bicyclobutanes (BCBs) and readily available enolate precursors. We propose this reaction proceeds via initial enolate addition to the bicyclobutane, followed by an intramolecular acyl substitution by the resulting enolate intermediate. Glycine-derived enolates directly give protected 2-oxo-3-amino-BCH derivatives that can be further functionalized. Arylacetate derivatives are also suitable enolate precursors, giving 2-oxo-3-aryl-BCH scaffolds from readily available starting materials.

Keywords

bioisosteres
bicyclobutane
bicyclohexane
enolate

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