Diethylzinc-Mediated Addition of 2,2-Dibromo-2-fluoroacetamides to Carbonyl Compounds: Synthesis of α-Bromo-α-fluoro-β-hydroxy Amides and/or (<i>Z</i>)-Fluorovinyl Amides
作者:Gérald Lemonnier、Thomas Poisson、Samuel Couve-Bonnaire、Philippe Jubault、Xavier Pannecoucke
DOI:10.1002/ejoc.201300140
日期:2013.6
We describe straightforward routes either to α-bromo-α-fluoro-β-hydroxy amides or to (Z)-α-fluoroacrylamides starting from aldehydes, ketones or imine and 2,2-dibromo-2-fluoroacetamides. Depending on the nature of the amide, these diethylzinc-mediated additions to aldehydes, ketones or imine afford selective access either to bromofluorohydrins or to (Z)-α-fluoroacrylamides. The corresponding products
我们描述了从醛、酮或亚胺和 2,2-二溴-2-氟乙酰胺开始的 α-溴-α-氟-β-羟基酰胺或 (Z)-α-氟丙烯酰胺的直接路线。根据酰胺的性质,这些二乙基锌介导的与醛、酮或亚胺的加成提供了对溴氟醇或 (Z)-α-氟丙烯酰胺的选择性访问。以中等至非常好的产率获得了相应的产品,两种产品的构型均通过 X 射线分析得到证实。