Cornerstones in Chemistry
Shi Epoxidation: A Great Shortcut to Complex Compounds
Xiangqing Feng,
Haifeng Du,
Xiangqing Feng
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorCorresponding Author
Haifeng Du
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 China
University of Chinese Academy of Sciences, Beijing, 100049 China
E-mail: [email protected]Search for more papers by this authorXiangqing Feng,
Haifeng Du,
Xiangqing Feng
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorCorresponding Author
Haifeng Du
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 China
University of Chinese Academy of Sciences, Beijing, 100049 China
E-mail: [email protected]Search for more papers by this authorAbstract
Shi epoxidation provides an extremely powerful tool to access optically active epoxides, which undoubtedly belongs to one of the earliest and most successful organocatalytic systems. Several generations of chiral ketones have been developed to realize the asymmetric epoxidation of each type of unfunctionalized alkenes, including trans-, trisubstituted olefins, cis-olefins, terminal olefins, and tetrasubstituted olefins. Due to its reliability and high regio- and enantioselectivity, Shi epoxidation has been widely applied in the synthesis of complex natural products and biologically active molecules.
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