Asymmetric strecker synthesis of alpha-amino acids via a crystallization-induced asymmetric transformation using (R)-phenylglycine amide as chiral auxiliary |
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| Authors: | Boesten W H Seerden J P de Lange B Dielemans H J Elsenberg H L Kaptein B Moody H M Kellogg R M Broxterman Q B |
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| Affiliation: | DSM Research Life Sciences-Organic Chemistry and Biocatalysis, P.O. Box 18, 6160 MD Geleen, and Syncom B.V., Kadijk 3, 9747 AT Groningen, The Netherlands. |
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| 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. |
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