340291-70-5Relevant articles and documents
Asymmetric strecker synthesis of α-amino acids via a crystallization-induced asymmetric transformation using (R)-phenylglycine amide as chiral auxiliary
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.
, p. 1121 - 1124 (2001)
Matrix presented 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.