American Chemical Society
ol5b02798_si_001.pdf (2.16 MB)

Stereoselective Construction of Bridged trans-aza-Bicyclo­[7/6,3/2,1]­alkenyl Imines through Ring Expansion aza-Cope Rearrangement

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journal contribution
posted on 2015-11-20, 00:00 authored by Mei-Hua Shen, Ke Xu, Chu-Han Sun, Hua-Dong Xu
A highly stereoselective method for efficient synthesis of unprecedented bridged bicyclo­[7/6,3/2,1]­alkenyl amidines is described using cyclic N-allyl-aminoalkyne as a substrate. A ketenimine formation/cyclization/aza-Cope rearrangement cascade proceeds either with or without the aid of external DIPEA depending on substrate basicity. Fused bicycloamidines are also obtained via the same protocol using different N-allyl cyclic aminoalkynes.