Diastereomeric fluoroolefins as peptide bond mimics prepared by asymmetric reductive amination of α-fluoroenones

被引:126
作者
Dutheuil, Guillaume [1 ]
Couve-Bonnaire, Samuel [1 ]
Pannecoucke, Xavier [1 ]
机构
[1] INSA Rouen, CNRS, UMR 6014, ECOFH,IRCOF, F-76131 Mont St Aignan, France
关键词
asymmetric synthesis; fluoroenones; fluoroolefins; peptidomimetics; reductive amination;
D O I
10.1002/anie.200604246
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Fluoropeptidomimetics: An efficient asymmetric reductive amination of fluoroenones has been developed that affords potential precursors of fluoropeptide isosteres. Stereoselective routes with different reductive agents provided both diastereomers from the same nonracemic sulfinyl imine. The method was applied to the synthesis of different dipeptide analogues. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1290 / 1292
页数:3
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