486407-81-2Relevant academic research and scientific papers
A regio- and stereodivergent route to all isomers of vic-amino alcohols.
Olofsson, Berit,Somfai, Peter
, p. 8574 - 8583 (2007/10/03)
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.
Aza-[3,3]-Claisen enolate rearrangement in vinylaziridines: Stereoselective synthesis of mono-, di-, and trisubstituted seven-membered lactams
Lindstroem, Ulf M.,Somfai, Peter
, p. 94 - 98 (2007/10/03)
Several 2,3-disubstituted vinylaziridines have been N-acylated and subjected to LiHMDS in THF at -78°C. Upon warming to room temperature, the resulting amide enolates underwent a highly stereoselective [3,3]-sigmatropic rearrangement to give mono-, di-, a
A regio-and stereodivergent synthesis of vic-amino alcohols
Olofsson, Berit,Khamrai, Uttam,Somfai, Peter
, p. 4087 - 4089 (2007/10/03)
(Matrix presented) A regio-and stereodivergent synthesis of vic-amino alcohols starting from vinylepoxides is described. The developed strategy focuses on the propensity of vinylepoxides and vinylaziridines to be ring-opened at the allylic position by sui
