Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Synthesis of Spirocyclic Amines by Using Dipolar Cycloadditions of Nitrones

Synthesis of Spirocyclic Amines by Using Dipolar Cycloadditions of Nitrones
Iain Coldham, Darren Collier, Rungroj Saruengkhanphasit
Aliphatic ketones containing a chloride and alkene were heated with hydroxylamine to promote cascade, tandem condensation to oximes, cyclization to nitrones, and 1,3-dipolar cycloaddition to tricyclic isoxazolidines as single stereoisomers. Single regioisomers were obtained when three atoms linked the ketone and dipolarophile to give five-membered rings but mixtures resulted with four atoms in the tether unless a terminal ester was located on the alkene. The N–O bond in the products could be reduced to give spirocyclic amines and diamines.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00959

DOI: 10.1021/acs.joc.7b00959

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