Synthesis of chiral β-3-amino-2-hydroxyalkanoates and 3-alkyl-3-hydroxy-β-lactams by double asymmetric induction |
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Authors: | Andrea Guerrini,Greta Varchi,Rizzo Daniele,Cristian Samorì ,Arturo Battaglia |
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Affiliation: | Istituto CNR per la Sintesi Organica e Fotoreattività—‘I.S.O.F.’, Area della Ricerca di Bologna, via P. Gobetti 101, 40129 Bologna, Italy |
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Abstract: | Reactions of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic, mandelic, and phenyllactic acids, with aliphatic (SS)- and (SR)-tert-butylsulfinyl aldimines afforded conformationally restrained C2-disubstituted N,O-orthogonally protected 3-amino-2-hydroxyalkanoates in the form of N-sulfinyl protected 1′-aminodioxolan-4-ones. The product distribution showed that there is significant kinetic selectivity, due to the presence of ‘matched’ and ‘mismatched’ components, between the (S)- or (R)-tert-butylsulfinyl aldimines and the (2S)-enolates of the 1,3-dioxolan-4-ones. Selective methoxide-induced removal of the acetal group of the N-sulfinyl-1′-aminodioxolanones yielded the corresponding N-sulfinyl protected methyl alkanoates. In addition, the selective acid-induced removal of the sulfinyl group of the N-sulfinyl-1′-aminodioxolanones provided the corresponding N-unprotected 1′-aminodioxolanones, whose base-induced cyclization afforded the corresponding β-lactams. |
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Keywords: | Dioxolan-4-ones Double asymmetric induction Aldimines α-Hydroxy-β-amino acids 3-Hydroxy-β-lactams |
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