173143-75-4Relevant academic research and scientific papers
A new route to functionalised π-allyltricarbonyliron lactam complexes from aziridines and their use in stereoselective synthesis and oxidative conversion to β-lactams
Ley, Steven V.,Middleton, Ben
, p. 1995 - 1996 (2007/10/03)
Aziridinyl enones can be converted in good yield into π-allyltricarbonyliron lactam complexes bearing ketone functionality in the side chain; addition of a variety of nucleophiles into the side chains of these complexes proceeds in good yield and excellen
Preparation and Use of Aziridino Alcohols as Promoters for the Enantioselective Addition of Dialkylzinc Reagents to N-(Diphenylphosphinoyl) Imines
Andersson, Pher G.,Guijarro, David,Tanner, David
, p. 7364 - 7375 (2007/10/03)
A set of chiral aziridino alcohols 2-5 has been synthesized starting from either readily available amino acids (L-serine, L-threonine, and allo-L-threonine) or simple olefins (using Sharpless asymmetric aminohydroxylation and dihydroxylation reactions). Chiral ligands 2-5 have been tested as promoters for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines 1. The influence of the substituants on the aziridine ring and the alcohol moiety on the selectivity has been studied, and in the best case, an enantiomeric excess of up to 94% could be obtained. Acidic hydrolysis of the initially formed N-protected amines 6 led to the corresponding free amines 7 without racemization. Although a stoichiometric amount of the ligand was used, about 90% of it could be recovered during the workup and reused without significant loss of chiral induction. The utility of the aziridino alcohols 2-5 as catalysts for the same reaction has also been evaluated and enantiomeric excesses of up to 76% were achieved using 0.25 equiv of the chiral ligand. A possible transition state for the addition reaction is also proposed.
