Carbohydrates as chiral templates: Stereoselective Strecker synthesis of D?螃窿?amino nitriles and acids using O??pivaloylated D??galactosylamine as the auxiliary

H Kunz, W Sager, D Schanzenbach…

Index: Kunz, Horst; Sager, Wilfried; Schanzenbach, Dirk; Decker, Mathias Liebigs Annalen der Chemie, 1991 , # 7 p. 649 - 654

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Citation Number: 67

Abstract

Abstract The asymmetric synthesis of N-galactosyl D-α-amino nitriles is accomplished by application of 2, 3, 4, 6-tetra-O-pivaloyl-β-D-galactopyranosylamine (4) as the stereodifferentiating template in Strecker reactions. Aldimines 6 derived from 4 and aromatic or aliphatic aldehydes react with trimethylsilyl cyanide in 2-propanol or tetrahydrofuran in the presence of Lewis acids, eg ZnCl 2 or SnCl 4′ to give the N-galactosyl α-amino nitriles 5 ...