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Facile evolution of asymmetric organocatalysts in water assisted by surfactant Brønsted acids
Authors:Sanzhong Luo  Hui Xu  Long Zhang  Xiaoxi Zheng
Institution:a Beijing National Laboratory for Molecular Sciences (BNLMS), Center for Chemical Biology, Institute of Chemistry, The Chinese Academy of Sciences, Beijing 100080, China
b Department of Chemistry and State-key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071,China
Abstract:Simple mixing of chiral amines and surfactant Brønsted acids such as p-dodecyl benzenesulfonic acid (DBSA) leads to highly effective and selective organocatalysts in water. The in situ generated catalysts catalyze highly stereoselective desymmetrization of prochiral ketones via direct aldol reactions (up to >16:1 dr, >99% ee) in water using micelle as reaction media. The current strategy was also applied in asymmetric Michael addition leading to a catalytic system with good activity and stereoselectivity.
Keywords:Aldol  Michael addition  Chiral amine  Surfactant Brø  nsted acids
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