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| 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 |
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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.
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Received: 05 January 2016
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2016, Vol. 24 
