Asymmetric Synthesis of Functionalized Bicyclic β??Amino Alcohols by Cascade Hydrometallation–Cyclization–Reduction of Glycinyl??Substituted Alkenylsulfoximines– …

S Acikalin, G Raabe, J Runsink…

Index: Acikalin, Serdar; Raabe, Gerhard; Runsink, Jan; Gais, Hans-Joachim European Journal of Organic Chemistry, 2011 , # 30 p. 5991 - 6008

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Abstract

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 ...