Stereoselective Synthesis of α,α’-Dihydroxy-β,β’-diaryl-β-amino Acids by Mannich-like Condensation of Hydroarylamides
Articolo
Data di Pubblicazione:
2019
Citazione:
Stereoselective Synthesis of α,α’-Dihydroxy-β,β’-diaryl-β-amino Acids by Mannich-like Condensation of Hydroarylamides / I. Pecnikaj, F. Foschi, R. Bucci, M.L. Gelmi, C. Castellano, F. Meneghetti, M. Penso. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 39:(2019 Oct 24), pp. 6707-6713. [10.1002/ejoc.201901325]
Abstract:
Dual α,α’-Dihydroxy-β-amino acids are very interesting tools for several industrial applications. Nevertheless, few derivatives are reported in the literature concerning the substitution pattern as well as their enantioselective syntheses are lacking. Here, we report on the preparation of enantiopure α,α’-dihydroxy-β,β’-diaryl-β-amino acid (dual) derivatives by an efficient Mannich-like condensation of hydroarylamides with 5,6-diethoxy-5,6-dimethyl-1,4-dioxan-2-one (triethylsilyl)ketene acetal. The synthetic protocol has been optimized affording the dual compounds in very good yields and with different aryl substitution patterns. Taking advantage of the “double stereodifferentiation” concept, a highly stereoselective reaction was performed: of the 16 possible isomers, only two diastereoisomers (d.r. up to 93:7) formed. Insights on the high stereocontrol of this condensation were given.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Diastereoselectivity; Enols; Mannich-like reaction; Hydroarylamides; Dual alfa,alfa'-hydroxy-beta-amino acids
Elenco autori:
I. Pecnikaj, F. Foschi, R. Bucci, M.L. Gelmi, C. Castellano, F. Meneghetti, M. Penso
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