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.

Lithiated three-membered heterocycles as chiral nucleophiles in the enantioselective synthesis of 1-oxaspiro[2,3]hexanes / Cocco, Andrea; Grazia Rubanu, Maria; Laura Sechi, Maria; Frongia, Angelo; Mastrorilli, Pietro; Degennaro, Leonardo; Colella, Marco; Luisi, Renzo; Secci, Francesco. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - STAMPA. - 19:9(2021), pp. 1945-1949. [10.1039/d0ob00771d]

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

Pietro Mastrorilli;
2021-01-01

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.
2021
Lithiated three-membered heterocycles as chiral nucleophiles in the enantioselective synthesis of 1-oxaspiro[2,3]hexanes / Cocco, Andrea; Grazia Rubanu, Maria; Laura Sechi, Maria; Frongia, Angelo; Mastrorilli, Pietro; Degennaro, Leonardo; Colella, Marco; Luisi, Renzo; Secci, Francesco. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - STAMPA. - 19:9(2021), pp. 1945-1949. [10.1039/d0ob00771d]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11589/224960
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