Applications of the sulfinimine-mediated asymmetric strecker synthesis to the synthesis of alpha-alkyl alpha-amino acids.
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.
Davis
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Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@astro.ocis.temple.edu
Lee
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Zhang
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Fanelli
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D000596:Amino Acids / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013452:Sulfonium Compounds / Q000737:chemistry*
D000596:Amino Acids; D007097:Imines; D013452:Sulfonium Compounds