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

…, B de Lange, HJA Dielemans, HLM Elsenberg…

Index: Boesten, Wilhelmus H. J.; Seerden, Jean-Paul G.; De Lange, Ben; Dielemans, Hubertus J. A.; Elsenberg, Henk L. M.; Kaptein, Bernard; Moody, Harold M.; Kellogg, Richard M.; Broxterman, Quirinus B. Organic Letters, 2001 , vol. 3, # 8 p. 1121 - 1124

Full Text: HTML

Citation Number: 56

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 ...