Morgan A J, Masse C E, Panek J S
Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, Massachusetts 02215, USA.
Org Lett. 1999 Dec 16;1(12):1949-52. doi: 10.1021/ol9903032.
[formula: see text] The asymmetric synthesis of beta-hydroxy-alpha-amino acids is reported which relies on the use of alpha,beta-unsaturated aryl ester substrates and the dihydroquinyl alkaloid ligand system (DHQ)2-AQN to control the regio- and enantioselectivity of the asymmetric aminohydroxylation (AA) process. alpha,beta-Unsaturated ester substrates of type 1 have a significant effect on the substrate-ligand recognition event which results in a reversal of regioselectivity in the AA reaction.
[化学式:见正文] 报道了β-羟基-α-氨基酸的不对称合成,该合成依赖于使用α,β-不饱和芳基酯底物和二氢喹啉生物碱配体体系(DHQ)₂-AQN来控制不对称氨基羟基化(AA)过程的区域选择性和对映选择性。1型α,β-不饱和酯底物对底物-配体识别事件有显著影响,这导致AA反应中区域选择性发生反转。