Synthesis of fluorinated pseudopeptides: metal mediated reversal of stereochemistry in diastereoselective addition of organometallic reagents to N-(tert-butanesulfinyl …

C Pierry, D Cahard, S Couve-Bonnaire…

文献索引：Pierry, Camille; Cahard, Dominique; Couve-Bonnaire, Samuel; Pannecoucke, Xavier Organic and Biomolecular Chemistry, 2011 , vol. 9, # 7 p. 2378 - 2386

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被引用次数: 20

摘要

The addition reaction of organometallic reagents to N-(tert-butanesulfinyl)-α-fluoroenimines was studied. Depending of the nature of the organometallic species (Grignard reagents or zincate complexes), we were able to control the configuration of the newly created stereogenic centers in high yields with good to high diastereomeric ratios. The chiral β-fluoro allylamines are key synthons toward the synthesis of fluorinated pseudopeptides bearing ...