Enantioselective addition of activated terminal alkynes to 1-acylpyridinium salts catalyzed by Cu-bis(oxazoline) complexes
Enantioselective addition of activated terminal alkynes to 1-acylpyridinium salts catalyzed by Cu-bis(oxazoline) complexes
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Cu-双(恶唑啉)配合物催化活性末端炔对映选择性加成至1-酰基吡啶鎓盐
DOI：
10.1021/ja0734849
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发表时间：
2007-08-01
影响因子：
15
通讯作者：
Ma, Dawei
中科院分区：
文献类型：
--
作者：
Sun, Zhankui;Yu, Shouyun;Ma, Dawei
在CuI/双恶唑啉催化下，1-酰基吡啶盐（由吡啶和氯甲酸甲酯原位反应生成）与丙炔酸酯和末端炔酮的加成反应，得到了高度官能化的二氢吡啶类化合物，具有良好的对映选择性.结果发现，羰基相邻的炔部分是必不可少的对映选择性的加成。吲哚嗪167 B和223 AB的短合成通过使用两个加成产物实现。
CuI/bis(oxazoline)-catalyzed addition of propiolates and terminal ynones to 1-acylpyridinium salt (generated in situ from reaction of pyridine and methyl chloroformate) affords highly functionalized dihydropyridines with excellent enantioselectivity. It is found that the carbonyl group adjacent to the alkyne moiety is essential for the enantioselectivity of the addition. Short synthesis of indolizidines 167B and 223AB is achieved by employing two addition products.