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  • Title: Construction of chiral α-amino quaternary stereogenic centers via phase-transfer catalyzed enantioselective α-alkylation of α-amidomalonates.
    Author: Ha MW, Lee M, Choi S, Kim S, Hong S, Park Y, Kim MH, Kim TS, Lee J, Lee JK, Park HG.
    Journal: J Org Chem; 2015 Mar 20; 80(6):3270-9. PubMed ID: 25675109.
    Abstract:
    An efficient enantioselective synthetic method for α-amido-α-alkylmalonates via phase-transfer catalytic α-alkylation was successfully developed. The α-alkylation of α-amidomalonates under phase-transfer catalytic conditions (50% KOH, toluene, -40 °C) in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide afforded the corresponding α-amido-α-alkylmalonates in high chemical yields (up to 99%) and optical yields (up to 97% ee), which could be readily converted to versatile chiral intermediates bearing α-amino quaternary stereogenic centers. The synthetic potential of this methodology was demonstrated via the synthesis of chiral azlactone, oxazoline, and unnatural α-amino acid.
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