Study of the reaction of imines derived from (R)-glyceraldehyde with Danishefsky's diene.
Study of the reaction of imines derived from (R)-glyceraldehyde with Danishefsky's diene.
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DOI：
10.1016/s0040-4020(99)00377-4
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发表时间：
1999-06-11
期刊：
影响因子：
2.1
通讯作者：
Gálvez, JA
中科院分区：
文献类型：
--
作者：
Badorrey, R;Cativiela, C;Gálvez, JA
在刘易斯酸存在下，由方便保护的（R）-甘油醛衍生的N-苄亚胺与Danishefsky二烯发生非对映选择性串联Mannich-Michael反应。描述了产物比率的温度、催化剂和溶剂依赖性。在碘化锌催化的条件下，在乙腈中，在-20 ℃下，使用（R）-2，3-二-O-苄基甘油醛（S）-N-α-（甲基苄基）亚胺作为起始原料的双立体分化是成功的，并且反应以良好的产率和完全的非对映选择性发生。(C)1999 Elsevier Science Ltd.保留所有权利。
N-Benzylimines derived from conveniently protected (R)-glyceraldehyde underwent diastereoselective tandem Mannich-Michael reaction with Danishefsky's diene in the presence of Lewis acids. The temperature, catalyst and solvent dependence of the product ratio is described. Under zinc iodide-catalysed conditions in acetonitrile at -20 degrees C, double stereodifferentiation using (R)-2,3-di-O-benzylglyceraldehyde (S)-N-alpha-(methylbenzyl)imine as starting material was successful and the reaction occurred with good yield and complete diastereoselectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.