Synthesis of (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic Acid Derivatives Catalyzed by D-proline
BAO Ke-ting1,2, ZHANG Wei2, LI Ying-xia2, HU Chun1
1.School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China; 2. School of Pharmacy, Fudan University, Shanghai 201203, China
Abstract：A new route for the synthesis of (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid derivatives 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 reaction, using amino-protected L-phenylalanine as starting material. The structures were confirmed by 1H NMR， 13C NMR and ESI-MS. The exploration of reaction conditions showed that the loading amount of D-proline had no evident effect on the yield, but on stereoselectivity. Larger size protecting groups in substrate can enhanced the stereoselectivity.
包可婷， 张伟， 李英霞， 胡春. 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[J]. 合成化学, 2016, 24(4): 355-358.
BAO Ke-ting, ZHANG Wei, LI Ying-xia, HU Chun. Synthesis of (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic Acid Derivatives Catalyzed by D-proline. Chinese Journal of Synthetic Chemistry, 2016, 24(4): 355-358.
2016, Vol. 24 
