Diethylzinc-Mediated Addition of 2,2-Dibromo-2-fluoroacetamides to Carbonyl Compounds: Synthesis of alpha-Bromo-alpha-fluoro-beta-hydroxy Amides and/or (Z)-Fluorovinyl Amides

作者：Lemonnier Gerald; Poisson Thomas; Couve Bonnaire Samuel; Jubault Philippe; Pannecoucke Xavier^*

来源：European Journal of Organic Chemistry, 2013, 2013(16): 3278-3289.

DOI：10.1002/ejoc.201300140

• Synthetic methods
• Fluorine
• Olefination
• Aldehydes

We describe straightforward routes either to alpha-bromo-alpha-fluoro-beta-hydroxy amides or to (Z)-alpha-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)-alpha-fluoroacrylamides. The corresponding products were obtained in moderate to very good yields and the configurations of both products were confirmed by X-ray analyses.

• 出版日期2013-6