The reaction between configurably stable alpha-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.
Lithiated three-membered heterocycles as chiral nucleophiles in the enantioselective synthesis of 1-oxaspiro[2,3]hexanes
Degennaro, Leonardo;Colella, Marco;Luisi, Renzo;
2021-01-01
Abstract
The reaction between configurably stable alpha-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.File in questo prodotto:
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