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Platinum-Catalyzed Michael Addition and Cyclization of Tertiary Amines with Nitroolefins by Dehydrogenation of α,β-sp3 C−H Bonds

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posted on 07.05.2010, 00:00 by Xiao-Feng Xia, Xing-Zhong Shu, Ke-Gong Ji, Yan-Fang Yang, Ali Shaukat, Xue-Yuan Liu, Yong-Min Liang
A mild platinum-catalyzed oxidative dehydrogenation of α,β-C(sp3)−H bonds of tertiary amines in the presence of ambient oxygen is revealed, and the in situ formed enamines subsequently reacting with various nitroolefins resulted in the development of two one-pot synthetic protocols involving Michael addition−elimination and Michael addition−cyclization. By using different functionalized nitroolefins compatible with the current oxidative conditions, two types of structurally divergent products, trisubstituted enamines and chromano[2,3-b]piperidines, could be expediently accessed, respectively.