Applications of the sulfinimine-mediated asymmetric strecker synthesis to the synthesis of alpha-alkyl alpha-amino acids |
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Authors: | Davis F A Lee S Zhang H Fanelli D L |
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Institution: | Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@astro.ocis.temple.edu |
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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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