54794-76-2Relevant academic research and scientific papers
Desymmetrization of meso-N-sulfonylaziridines with chiral nonracemic nucleophiles and bases
Mueller, Paul,Nury, Patrice
, p. 662 - 677 (2007/10/03)
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.
