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

Wilhelmus H.J. Boesten, Jean-Paul G. Seerden, Ben de Lange, Hubertus J.A. Dielemans, Henk L.M. Elsenberg, Bernard Kaptein, Harold M. Moody, Richard M. Kellogg, Quirinus B. Broxterman

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Abstract

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 α-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.
Original languageEnglish
Number of pages4
JournalOrganic letters
Volume3
Issue number8
DOIs
Publication statusPublished - 2001

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