Chiral tetraaminophosphonium salt-mediated asymmetric direct Henry reaction.

Chiral tetraaminophosphonium salt-mediated asymmetric direct Henry reaction.
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DOI:
10.1021/ja075152
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发表时间:
2007-09
影响因子:
15
通讯作者:
D. Uraguchi;S. Sakaki;T. Ooi
D. Uraguchi;S. Sakaki;T. Ooi
中科院分区:
化学1区
文献类型:
--
作者:
D. Uraguchi;S. Sakaki;T. Ooi

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以L-缬氨酸二胺为原料,设计并一步合成了具有磷中心螺环核心的手性四氨基膦盐1。单晶X-射线衍射分析证实了该化合物的三维分子结构,证实了阳离子与氯离子之间通过双氢键的二次相互作用。在不对称直接Henry反应中,这种新型有机盐作为手性有机分子催化剂的潜力已被证明。
Chiral tetraaminophosphonium salts 1 possessing the phosphorus-centered [5.5]-spirocyclic core have been designed and synthesized in a single step from l-valine-derived diamine. The three-dimensional molecular structure was successfully verified by the single-crystal X-ray diffraction analysis, which also identified a secondary interaction between the phosphonium cation and chloride ion via double hydrogen-bonding. The potential of this novel onium salt as a chiral organic molecular catalyst has been demonstrated in an application to asymmetric direct Henry reaction.