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Synthesis, Characterization and Application of Some Axially Chiral Binaphthyl Phosphoric Acids in Asymmetric Mannich Reaction
Author(s) -
Yao Yuanyong,
Shu Hua,
Tang Bangcheng,
Chen Shixue,
Lu Zhongying,
Xue Wei
Publication year - 2015
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201500017
Subject(s) - chemistry , phosphoric acid , catalysis , mannich reaction , yield (engineering) , enantiomer , enantiomeric excess , organic chemistry , brønsted–lowry acid–base theory , diol , axial symmetry , enantioselective synthesis , materials science , structural engineering , engineering , metallurgy
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.