An easy approach to optically active α-amino phosphonic acid derivatives by chiral Zn(II)-catalyzed enantioselective amination of phosphonates

被引:103
作者
Bernardi, L
Zhuang, W
Jorgensen, KA [1 ]
机构
[1] Aarhus Univ, Ctr Catalysis, Dept Chem, Danish Natl Res Fdn, DK-8000 Aarhus, Denmark
[2] Fac Chim Ind, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
关键词
D O I
10.1021/ja050989v
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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. Copyright © 2005 American Chemical Society.
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页码:5772 / 5773
页数:2
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