Advanced Synthesis and Catalysis
Advanced Synthesis and Catalysis
5 years ago

Organocatalytic Enantioselective Synthesis of Dihydropyrano- indole Derivatives Bearing Trifluoromethylated All-Carbon- Substituted Stereocenters

Organocatalytic Enantioselective Synthesis of Dihydropyrano- indole Derivatives Bearing Trifluoromethylated All-Carbon- Substituted Stereocenters
Guokai Liu, Yuyang Ding, Junling Zhao, Qinxin Lou, Dengfeng Xu
Malononitrile and isatin-derived trifluoromethylacrylates underwent a Michael addition/cyclization reaction, a process that was catalyzed efficiently by a bifunctional squaramide to afford a range of dihydropyranoindole derivatives bearing trifluoromethylated all-carbon-substituted stereocenters in high yields (up to 99%) with excellent enantioselectivity (up to 98% ee). This transformation was also examined with ethyl cyanoacetate as a nucleophile using a bifunctional thiourea as catalyst affording moderate yields (up to 79%) and high enantioselectivity (up to 98% ee). One of the products has been used for the synthesis of a biologically interesting triazolopyrimidine derivative.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adsc.201700465

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