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1. Asymmetric Strecker Synthesis of α-Amino Acids via a Crystallization-Induced Asymmetric Transformation Using (R)-Phenylglycine Amide as Chiral Auxiliary

Author

Quirinus B. Broxterman, Hubertus Johannes Adrianus Dielemans, Henk Elsenberg, Richard M. Kellogg, Bernard Kaptein, Ben De Lange, Jean-Paul G. Seerden, Wilhelmus H. J. Boesten, Harold Monro Moody, and Stratingh Institute of Chemistry

Subjects
Models, Molecular, chemistry.chemical_classification, Chiral auxiliary, Magnetic Resonance Spectroscopy, Nitrile, Stereochemistry, Organic Chemistry, Strecker amino acid synthesis, Glycine, Temperature, Diastereomer, Stereoisomerism, Crystallography, X-Ray, Amides, Biochemistry, Amino acid, chemistry.chemical_compound, Models, Chemical, chemistry, Amide, Yield (chemistry), Amino Acids, Physical and Theoretical Chemistry, Crystallization
Abstract

[reaction: see text]. Diastereoselective Strecker reactions based on (R)-phenylglycine amide as chiral auxiliary are reported. The Strecker reaction is accompanied by an in situ crystallization-induced asymmetric transformation, whereby one diastereomer selectively precipitates and can be isolated in 76-93% yield and dr > 99/1. The diastereomerically pure alpha-amino nitrile obtained from pivaldehyde (R1 = t-Bu, R2 = H) was converted in three steps to (S)-tert-leucine in 73% yield and >98% ee.

Published
2001

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