E-viri
Recenzirano
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Cocco, Andrea; Rubanu, Maria Grazia; Sechi, Maria Laura; Frongia, Angelo; Mastrorilli, Pietro; Degennaro, Leonardo; Colella, Marco; Luisi, Renzo; Secci, Francesco
Organic & biomolecular chemistry, 03/2021, Letnik: 19, Številka: 9Journal Article
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. Enantiomerically enriched oxaspiro- and azaspirohexanes were synthesized through a two-step addition of configurably stable Li-styrene oxide (or aziridine) to 3-substituted cyclobutanones and base-mediated Payne rearrangement sequence with high yields and selectivity.
