Highly active chiral Phosphoramide-Zn(II) complexes as conjugate acid-base catalysts for enantioselective organozinc addition to ketones
Highly active chiral Phosphoramide-Zn(II) complexes as conjugate acid-base catalysts for enantioselective organozinc addition to ketones
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DOI：
10.1021/ol702074a
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发表时间：
2007-10-25
期刊：
影响因子：
5.2
通讯作者：
Ishihara, Kazuaki
中科院分区：
文献类型：
--
作者：
Hatano, Manabu;Miyamoto, Takashi;Ishihara, Kazuaki
开发了一种高效的手性磷酰胺-Zn（II）配合物（1-10 mol %）催化的有机锌（R2 Zn）与酮的对映选择性加成反应。这些络合物用作共轭刘易斯酸-刘易斯碱催化剂。手性磷酰胺衍生自廉价的天然氨基酸（即，L-缬氨酸）。在温和的反应条件下，由各种未活化的芳香酮和脂肪酮，以高产率和高的对映选择性（高达98%ee）得到了相应的光学活性叔醇。
[GRAPHICS]A highly efficient enantioselective organozinc (R2Zn) addition to ketones catalyzed by chiral phosphoramide-Zn(II) complexes (1-10 mol %) has been developed. These complexes serve as conjugate Lewis acid-Lewis base catalysts. Chiral phosphoramides are derived from an inexpensive natural amino acid (i.e., L-valine). From a variety of nonactivated aromatic and aliphatic ketones, the corresponding optically active tertiary alcohols were obtained in high yields with high enantioselectivities (up to 98% ee) under the mild reaction conditions.