Preparation of enantiomerically pure 9-azabicyclo[3,3,1]nonene derivatives. Stereochemical requirements of vinyl- and allylsilanes in iminium ion initiated cyclization

Article abstract of DOI:10.1016/0040-4039(95)00411-5

Asymmetric synthesis of the 9-azabicyclo[3,3,1]nonene skeleton of granatanine has been achieved through the cyclization of non-racemic (Z)-vinylsilane oxazolidine (Z)-2, an iminium ion precursor. The corresponding (E)-isomer (E)-2 did not cyclize in the s