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

Cocco A.;Rubanu M. G.;Sechi M. L.;Frongia A.;Mastrorilli P.;Degennaro L.;Colella M.;Luisi R.;Secci F.

2021-01-01

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Abstract

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.