Lithiated three-membered heterocycles as chiral nucleophiles in the enantioselective synthesis of 1-oxaspiro[2,3]hexanes.
Andrea CoccoMaria Grazia RubanuMaria Laura SechiAngelo FrongiaPietro MastrorilliLeonardo DegennaroMarco ColellaRenzo LuisiFrancesco SecciPublished in: Organic & biomolecular chemistry (2021)
The reaction between configurably stable α-lithiated oxiranes and 3-substituted cyclobutanones allows obtaining enantiomerically enriched cyclobutanols (er > 98 : 2). These adducts, subjected to base-mediated Payne rearrangement, lead to the synthesis of a new class of oxaspirohexanes, useful precursors of 2,4-disubstituted cyclopentanones.