Enolate addition to bicyclobutanes enables expedient access to 2-oxo-bicyclohexane scaffolds
Kyla Woelk, Kushal Dhake, Nathan D. Schley, David C. Leitch
Abstract
We report the synthesis of 2-oxo-bicyclo[2.1.1]hexanes (2-oxo-BCHs) from bicyclobutanes (BCBs) and readily available enolate precursors. 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.
Topics & Concepts
ChemistryComputer scienceChemical Synthesis and AnalysisAsymmetric Hydrogenation and CatalysisCyclopropane Reaction Mechanisms