School of Chemistry and Chemical Engineering, Beijing Institute of Technology, 5 South Zhongguancun Street, Beijing 100081, P. R. China.
Org Biomol Chem. 2019 Aug 14;17(30):7182-7191. doi: 10.1039/c9ob01350d. Epub 2019 Jul 19.
An enantioselective Mannich reaction between 3-fluorooxindoles and pyrazolinone ketimines has been developed for the construction of amino-pyrazolone-oxindoles containing stereogenic C-F units. Based on this new protocol that allows for the generation of two adjacent tetrasubstituted stereocenters, a variety of structurally diverse fluorinated amino-pyrazolone-oxindoles were obtained in good to excellent yields with excellent diastereoselectivities and enantioselectivities (up to 98% yield, >20 : 1 dr and >99% ee). What's more, good yield and high stereoselectivities were obtained in the gram-scale reaction.
已开发出一种 3-氟色酮与吡唑啉酮亚胺之间的对映选择性 Mannich 反应，用于构建含有手性 C-F 单元的氨基-吡唑啉酮-色酮。基于此新方案，可以生成两个相邻的四取代立体中心，通过该方案获得了多种结构多样的氟化氨基-吡唑啉酮-色酮，收率良好至优秀，具有极好的非对映选择性和对映选择性（高达 98%的收率，>20:1 dr 和>99%ee）。更重要的是，在克级反应中也获得了良好的收率和高立体选择性。
