Copper‐Catalyzed Oxidative Dimerizations of 3‐N‐Hydroxy‐aminoprop‐1‐enes to form 1,4‐Dihydroxy‐2,3‐diaminocyclohexanes with C2 Symmetry |
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Authors: | Satish Ghorpade Prof. Dr. Rai‐Shung Liu |
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Affiliation: | Department of Chemistry, National Tsing Hua University, 101, Sec. 2, Kuang‐Fu Rd., Hsinchu 30013 (Taiwan) http://chem‐en.web.nthu.edu.tw/files/13‐1117‐33454.php |
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Abstract: | This work describes the one‐step construction of complex and important molecular frameworks through copper‐catalyzed oxidations of cheap tertiary amines. Copper‐catalyzed aerobic oxidations of N‐hydroxyaminopropenes to form C2‐symmetric N‐ and O‐functionalized cyclohexanes are described. Such catalytic oxidations proceed with remarkable stereocontrol and high efficiency. Reductive cleavage of the two N? O bonds of these products delivers 1,4‐dihydroxy‐2,3‐diaminocyclohexanes, which are important skeletons of several bioactive molecules. |
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Keywords: | copper cyclization oxidation radicals synthetic methods |
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