Diastereoselective Strecker reaction of D-glyceraldehyde derivatives. A novel route to (2S,3S)- and (2R,3S)-2-amino-3,4-dihydroxybutyric acid.
Diastereoselective Strecker reaction of D-glyceraldehyde derivatives. A novel route to (2S,3S)- and (2R,3S)-2-amino-3,4-dihydroxybutyric acid.
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DOI：
10.1016/0040-4020(96)00493-0
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发表时间：
1996-07-08
期刊：
影响因子：
2.1
通讯作者：
Garcia, JI
中科院分区：
文献类型：
--
作者：
Cativiela, C;DiazdeVillegas, MD;Garcia, JI
利用立体选择性Strecker型反应，由适当保护的D-甘油醛衍生的羰基化合物合成了对映体纯的（2S，3S）-和（2 R，3S）-2-氨基-3，4-二羟基丁酸。氰化物加成的立体选择性取决于金属络合剂的存在，这在（2 R）-2，3-二-O-苄基-D-甘油醛的情况下是必要的。此外，理论计算，以合理化的立体化学过程的反应已经进行。版权所有（C）1996 Elsevier Science Ltd
Efficient and stereoselective synthetic routes to enantiomerically pure (2S,3S)- and (2R,3S)-2-amino-3,4-dihydroxybutyric acid have been developed using the stereoselective Strecker type reaction of carbonyl compounds derived from appropriately protected D-glyceraldehyde. The stereoselectivity of the cyanide addition was shown to be dependent on the presence of metal complexing agents, which is essential in the case of (2R)-2,3-di-O-benzyl-D-glyceraldehyde. In addition, theoretical calculations to rationalize the stereochemical course of the reaction have been performed. Copyright (C) 1996 Elsevier Science Ltd