An easy approach to optically active α-amino phosphonic acid derivatives by chiral Zn(II)-catalyzed enantioselective amination of phosphonates
An easy approach to optically active α-amino phosphonic acid derivatives by chiral Zn(II)-catalyzed enantioselective amination of phosphonates
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DOI：
10.1021/ja050989v
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发表时间：
2005-04-27
影响因子：
15
通讯作者：
Jorgensen, KA
中科院分区：
文献类型：
--
作者：
Bernardi, L;Zhuang, W;Jorgensen, KA
以手性双恶唑啉锌（II）配合物为催化剂，研究了β-酮基膦酸酯的直接对映选择性亲电胺化反应.该反应进行良好的无环和环状底物在高产率和高达98%ee使用偶氮二羧酸作为氮源。反应的范围是，例如，进一步转化为具有非常高立体选择性的光学活性β-羟基−α-氨基膦酸酯。
A catalytic direct enantioselective electrophilic amination of β-keto phosphonates has been developed applying chiral bisoxazoline−zinc(II) complexes as the catalyst. The reaction proceeds well for both acyclic and cyclic substrates in high yields and with up to 98% ee using azodicarboxylates as the nitrogen source. The scope of the reaction is, for example, the further transformation to optically active β-hydroxy−α-amino phosphonates with very high stereoselection.