Magnesium-tartramide complex mediated asymmetric Strecker-type reaction of nitrones using cyanohydrin.
Magnesium-tartramide complex mediated asymmetric Strecker-type reaction of nitrones using cyanohydrin.
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DOI：
10.1021/ol400898p
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发表时间：
2013-05
期刊：
影响因子：
5.2
通讯作者：
Takahiro Sakai;T. Soeta;K. Endo;S. Fujinami;Y. Ukaji
中科院分区：
文献类型：
--
作者：
Takahiro Sakai;T. Soeta;K. Endo;S. Fujinami;Y. Ukaji
以丙酮合氰化氢为HCN源，实现了硝酮的不对称Strecker型反应。由（R，R）-2，3-二羟基-1，4-二（吡咯烷-1-基）丁烷-1，4-二酮与MeMgBr生成的镁-酒石酰胺络合物，在催化量的DBU存在下，促进氰醇的溴镁盐的转氰反应，得到相应的光学活性的（S）-α-氨基腈衍生物。该反应适用于各种硝酮，具有很高的对映选择性。
An asymmetric Strecker-type reaction of nitrones using acetone cyanohydrin as a source of HCN has been realized. A magnesium-tartramide complex, generated from (R,R)-2,3-dihydroxy-1,4-di(pyrrolidin-1-yl)-butane-1,4-dione and MeMgBr, promoted transcyanation from the bromomagnesium salt of the cyanohydrin, in the presence of a catalytic amount of DBU, to afford the corresponding optically active (S)-α-amino nitrile derivatives. The reaction was applicable to various nitrones giving high-to-excellent enantioselectivities.