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Copper‐Catalyzed Oxidative Dimerizations of 3‐ N ‐Hydroxy‐aminoprop‐1‐enes to form 1,4‐Dihydroxy‐2,3‐diaminocyclohexanes with C 2 Symmetry
Author(s) -
Ghorpade Satish,
Liu RaiShung
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201407987
Subject(s) - chemistry , cyclohexanes , catalysis , copper , oxidative cleavage , molecule , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry
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 C 2 ‐symmetric N‐ and O‐functionalized cyclohexanes are described. Such catalytic oxidations proceed with remarkable stereocontrol and high efficiency. Reductive cleavage of the two NO bonds of these products delivers 1,4‐dihydroxy‐2,3‐diaminocyclohexanes, which are important skeletons of several bioactive molecules.