(S)-Mandelic acid enolate as a chiral benzoyl anion equivalent for the enantioselective synthesis of non-symmetrically substituted benzoins |
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Authors: | Gonzalo BlayIsabel Fernández Belén MonjeMarc Montesinos-Magraner José R Pedro |
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Institution: | Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, E-46100 Burjassot, València, Spain |
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Abstract: | A strategy for the enantioselective synthesis of non-symmetrically substituted benzoins from (S)-mandelic acid and aromatic aldehydes has been developed. This strategy is based on a diastereoselective aldol reaction of the lithium enolate of the 1,3-dioxolan-4-one derived from (S)-mandelic acid and pivalaldehyde with aromatic aldehydes, which gives the corresponding aldols in good yields. Subsequent hydroxyl group protection as MEM ethers, basic hydrolysis of the dioxolanone ring, oxidative decarboxylation of the α-hydroxy acid moiety, and hydroxyl group deprotection provides chiral non-symmetrically substituted benzoins with high enantiomeric excesses. |
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Keywords: | Umpolung Aldol reaction Dioxolanone Hydroxy ketones Decarboxylation |
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