Masumoto Shuji, Usuda Hiroyuki, Suzuki Masato, Kanai Motomu, Shibasaki Masakatsu
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.
J Am Chem Soc. 2003 May 14;125(19):5634-5. doi: 10.1021/ja034980+.
A new method for the catalytic enantioselective Strecker reaction (cyanation) of N-diphenylphosphinoyl ketoimines is described. The asymmetric catalyst is a chiral gadolinium complex prepared from Gd(OiPr)3 and the d-glucose-derived ligand 3 in a 1:2 ratio. The reaction has a broad substrate generality, giving high enantioselectivity from aromatic, ethyl, primary alkyl, and alpha,beta-unsaturated ketoimines. The products could be easily converted to disubstituted alpha-amino acids and their derivatives.
描述了一种用于N-二苯基膦酰基酮亚胺的催化对映选择性Strecker反应（氰化反应）的新方法。不对称催化剂是由Gd(OiPr)3和d-葡萄糖衍生的配体3以1:2的比例制备的手性钆配合物。该反应具有广泛的底物通用性，对于芳香族、乙基、伯烷基和α,β-不饱和酮亚胺能给出高对映选择性。产物能够容易地转化为二取代的α-氨基酸及其衍生物。
