Lithiated three-membered heterocycles as chiral nucleophiles in the enantioselective synthesis of 1-oxaspiro[2,3]hexanes.

The reaction between configurably stable -lithiated oxiranes (and aziridines) and 3-substituted cyclobutanones allows to obtain 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.