Abstract
Annulated Aminocyclopropane-endo-carbonitriles 11a,b are reductively decyanated by sodium in liquid ammonia with complete retention of configuration. An additionally existing chlorine atom in the starting materials 12a,c–e, thereby, is simulataneously replaced by hydrogen. The preparative advantage of this method is demonstrated by the selective access to 6α-H-isomers 13b and 13e as members of the ensemble of bicyclo[3.1.0]hexanediyl-dimorpholine diastereomers. A strong buckled bicyclohexane unit is present in 3α,6αisomer 13e as indicated by 1H NMR spectroscopy and X-ray structural analysis.
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