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  • Title: Applications of the sulfinimine-mediated asymmetric strecker synthesis to the synthesis of alpha-alkyl alpha-amino acids.
    Author: Davis FA, Lee S, Zhang H, Fanelli DL.
    Journal: J Org Chem; 2000 Dec 15; 65(25):8704-8. PubMed ID: 11112592.
    Abstract:
    Addition of Et(2)AlCN and i-PrOH to ketosulfinimines (N-sulfinyl imines) affords corresponding alpha-alkyl alpha-amino nitriles in moderate to good yields. The diastereoselectivity is largely dependent on the E/Z isomer ratio of the ketosulfinimine. Hydrolysis of the diastereomerically pure amino nitriles affords enantiopure alpha-alkyl alpha-amino acids in moderate to good yields.
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