Enantioselective Henry (nitroaldol) reaction catalyzed by axially chiral guanidines.
Enantioselective Henry (nitroaldol) reaction catalyzed by axially chiral guanidines.
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DOI：
10.1016/j.bmcl.2009.03.097
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发表时间：
2009-07
影响因子：
2.7
通讯作者：
H. Ube;M. Terada
中科院分区：
文献类型：
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作者：
H. Ube;M. Terada
基于手性胍与硝酸根通过两个氢键的络合作用，尝试了硝基烷烃的对映选择性活化。以轴向手性金刚烷碱为催化剂，将所提出的对映体选择性活化方法应用于硝基烷烃与醛的非对映和对映选择性Henry(硝基醛)反应。在较低的温度下，以可接受的产率获得了光学活性的硝醛产品，并具有较好的对映和非对映选择性。
The enantioselective activation of nitroalkanes was attempted on the basis of the complexation between chiral guanidinium and nitronate through two hydrogen bonds. The proposed enantioselective activation was applied to the diastereo- and enantioselective Henry (nitroaldol) reaction of nitroalkanes with aldehydes using axially chiral guanidine bases as the catalyst. Optically active nitroaldol products were obtained in acceptable yields with fairly good enantio- and diastereoselectivities at low temperature.