A regio- and stereodivergent route to all isomers of vic-amino alcohols.
Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.
Olofsson
Berit
B
Department of Chemistry, Organic Chemistry, Royal Institute of Technology, S-100 44 Stockholm, Sweden.
Somfai
Peter
P
D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006868:Hydrolysis; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
D000605:Amino Alcohols; D014753:Vinyl Compounds