Applications of the Sulfinimine-Mediated Asymmetric Strecker Synthesis to the Synthesis of α-Alkyl α-Amino Acids
The Journal of Organic Chemistry2000Vol. 65(25), pp. 8704–8708
Citations Over TimeTop 10% of 2000 papers
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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