D-脯氨酸催化的(3S,4S)-4-氨基-3-羟基-5-苯基戊酸衍生物的合成

报道了一条合成(3S,4S)-4-氨基-3-羟基-5-苯基戊酸(Ahppa)衍生物的新路线。以氨基保护的L-苯丙氨酸为起始原料，依次经Weinreb胺缩合、还原、aldol缩合及溴仿4步反应合成了3个Ahppa衍生物，总收率5.8%~6.7%，其结构经¹H NMR， ¹³C NMR和ESI-MS确证。对反应条件进行了探讨，结果表明：催化剂D-脯氨酸用量对反应收率影响不大，对立体选择性影响较大；氨基上保护基体积较大有利于提高反应立体选择性。

Synthesis of ( 3 S,4 S)-4-amino-3-hydroxy-5-phenylpentanoic Acid Derivatives Catalyzed by D-proline

A new route for the synthesis of (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid deriv-atives was reported.The target compounds with overall yields of 5.8%~6.7% were synthesized by condensation with Weinreb amide, reduction, aldol condensation reaction and bromine imitation reac-tion, using amino-protected L-phenylalanine as starting material.The structures were confirmed by 1 H NMR, 13 C NMR and ESI-MS.The exploration of reaction conditions showed that the loading a-mount of D-proline had no evident effect on the yield, but on stereoselectivity.Larger size protecting groups in substrate can enhanced the stereo-selectivity.