Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N-Boc ketimines catalyzed by chiral phase-transfer catalysts

作者：Liu, Yuxin; Wang, Jingdong; Wei, Zhonglin; Cao, Jungang; Liang, Dapeng; Lin, Yingjie^*; Duan, Haifeng^*

来源：New Journal of Chemistry, 2018, 42(3): 1608-1611.

DOI：10.1039/c7nj04527a

• AZA-HENRY REACTION
• CYCLIC TRIFLUOROMETHYL KETIMINES
• HIGHLY EFFICIENT
• ASYMMETRIC-SYNTHESIS
• MICHAEL ADDITION
• BIFUNCTIONAL ORGANOCATALYST
• CINCHONA ALKALOIDS
• BEARING
• CONSTRUCTION
• DERIVATIVES

A highly diastereo- and enantioselective nitro-Mannich reaction of isatin-derived ketimines with alpha-aryl nitromethane catalyzed by Cinchona alkaloid-derived phase-transfer catalysts bearing multiple hydrogen-bonding donors (the first metal-free catalytic systems used in this reaction) was developed. A series of 3-substituted 3-amino-oxindoles were constructed using this protocol in excellent yields (96-99%) with high enantioselectivities (up to 95% ee) and diastereo-selectivities (up to 95:5 dr).

• 出版日期2018-2-7
• 单位吉林大学