No abstract

The treatment of exocyclic alkenylsulfoximines, which carry an α-glycinyl group at the allylic position, with HAliBu 2 caused cascade hydroalumination-cyclization-reduction and delivered the corresponding enantio-and diastereopure sulfoximine-substituted bicyclic β-amino alcohols with a bicyclo[3.3.0]octane and bicyclo[4.3.0]nonane skeleton in high yields. Three consecutive stereogenic C atoms of the bicyclic β-amino alcohols were generated in the cascade reactions with high diastereoselectivities. Application of the hydroalumination-cyclization-reduction to a ketal-substituted sixmembered exocyclic alkenylsulfoximine afforded the corresponding sulfoximine-substituted β-amino alcohol with a ketal-functionalized bicyclo[4.3.0]nonane skeleton. Reduction of a sulfoximine-substituted β-amino alcohol gave the parent β-amino alcohol, whereas its oxidative deamination afforded the corresponding sulfonyl-substituted β-amino alcohol. The