Asymmetric strecker synthesis of alpha-amino acids via a crystallization-induced asymmetric transformation using (R)-phenylglycine amide as chiral auxiliary

W H Boesten; J P Seerden; B de Lange; H J Dielemans; H L Elsenberg; B Kaptein; H M Moody; R M Kellogg; Q B Broxterman

doi:10.1021/ol007042c

Asymmetric strecker synthesis of alpha-amino acids via a crystallization-induced asymmetric transformation using (R)-phenylglycine amide as chiral auxiliary

Org Lett. 2001 Apr 19;3(8):1121-4. doi: 10.1021/ol007042c.

Authors

W H Boesten¹, J P Seerden, B de Lange, H J Dielemans, H L Elsenberg, B Kaptein, H M Moody, R M Kellogg, Q B Broxterman

Affiliation

¹ 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.

PMID: 11348174
DOI: 10.1021/ol007042c

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.

MeSH terms

Amides / chemistry*
Amino Acids / chemical synthesis*
Crystallization*
Crystallography, X-Ray
Glycine / analogs & derivatives
Glycine / chemistry*
Magnetic Resonance Spectroscopy
Models, Chemical
Models, Molecular
Stereoisomerism
Temperature

Substances

Amides
Amino Acids
N-phenylglycine
Glycine