Synthesis, Characterization and Application of Some Axially Chiral Binaphthyl Phosphoric Acids in Asymmetric Mannich Reaction
Yuanyong Yao
Institute of Material and Chemical Engineering, Tongren University, Tongren, Guizhou 554300, China
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, Guizhou 550025, China
Search for more papers by this authorHua Shu
Institute of Material and Chemical Engineering, Tongren University, Tongren, Guizhou 554300, China
Search for more papers by this authorBangcheng Tang
Institute of Material and Chemical Engineering, Tongren University, Tongren, Guizhou 554300, China
Search for more papers by this authorShixue Chen
Institute of Material and Chemical Engineering, Tongren University, Tongren, Guizhou 554300, China
Search for more papers by this authorZhongying Lu
Institute of Material and Chemical Engineering, Tongren University, Tongren, Guizhou 554300, China
Search for more papers by this authorCorresponding Author
Wei Xue
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, Guizhou 550025, China
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, Guizhou 550025, China, Tel.: 0086-0851-8292920; Fax: 0086-0851-8292920Search for more papers by this authorYuanyong Yao
Institute of Material and Chemical Engineering, Tongren University, Tongren, Guizhou 554300, China
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, Guizhou 550025, China
Search for more papers by this authorHua Shu
Institute of Material and Chemical Engineering, Tongren University, Tongren, Guizhou 554300, China
Search for more papers by this authorBangcheng Tang
Institute of Material and Chemical Engineering, Tongren University, Tongren, Guizhou 554300, China
Search for more papers by this authorShixue Chen
Institute of Material and Chemical Engineering, Tongren University, Tongren, Guizhou 554300, China
Search for more papers by this authorZhongying Lu
Institute of Material and Chemical Engineering, Tongren University, Tongren, Guizhou 554300, China
Search for more papers by this authorCorresponding Author
Wei Xue
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, Guizhou 550025, China
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, Guizhou 550025, China, Tel.: 0086-0851-8292920; Fax: 0086-0851-8292920Search for more papers by this authorAbstract
Two novel chiral Br?nsted acids 3b and 3c were prepared without involving the complexity of Suzuki coupling. Catalyst 3c bearing two additional hydroxyl groups at 3 and 3′ positions of axially chiral 1,1-binaphthalene-2,2′-diol phosphoric acid was applied in a model Mannich reaction to afford β-amino ester in high yield (92%) and enantiomeric excess (91%) at low reacting temperature of −40°C. In addition, those β-amino ester derivatives with high yields and excellent enatioselectivities were obtained in the presence of catalyst 3c under the above condition.
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