155631-48-4Relevant articles and documents
Desymmetrization of meso-N-sulfonylaziridines with chiral nonracemic nucleophiles and bases
Mueller, Paul,Nury, Patrice
, p. 662 - 677 (2001)
The cyclohexene-derived aziridine 7-tosyl-7-azabicyclo[4.1.0]heptane (1) reacts with Grignard reagents in the presence of chiral nonracemic Cu-catalysts to afford sulfonamides 3a-e in up to 91% ee under optimized conditions. No activation of the aziridine by Lewis acids is required. The reaction may be extended to other bicyclic N-sulfonylated aziridines, but aziridines derived from acyclic olefins, cyclooctene, and trinorbornene are unreactive under standard conditions. Exposure of 1 to s-BuLi in the presence of (-)-sparteine (2.8 equiv.) affords the allylic sulfonamide 31 in 35% yield and 39% ee. Under the same conditions, the aziridines 33 and 35 yield products 34 and 36 derived from intramolecular carbenoid insertion with 75 and 43% ee, respectively.
Enantiomerically pure oxazolines tethered to alcohols. Preparation and use in asymmetric catalysis
Allen,Williams
, p. 277 - 282 (2007/10/02)
A series of enantiomerically pure oxazolines tethered to alcohols have been prepared. The use of these oxazolines has been demonstrated in the catalysed addition of diethylzine to aromatic aldehydes to afford the corresponding secondary alcohols with modest levels of asymmetric induction.
