78477-91-5Relevant academic research and scientific papers
Chiral fluoro ketones for catalytic asymmetric epoxidation of alkenes with oxone
Denmark, Scott E.,Matsuhashi, Hayao
, p. 3479 - 3486 (2007/10/03)
Two structurally dissimilar, chiral fluoro ketones have been prepared and their potential as enantioselective catalysts for asymmetric epoxidation with Oxone has been evaluated. The tropinone-based ketone (-)-5 was easily prepared and showed excellent reactivity but only modest enantioselectivity. The biphenyl-based ketone (-)-6 was prepared in a somewhat lengthy synthesis (along with its monofluoro and geminal fluoro analogues). This ketone exhibited only modest reactivity; 30 mol % of (-)-6 was needed to bring about complete conversion in a reasonable time. The enantioselectivity of this catalyst was generally much higher, but again very substrate dependent.
A facile and efficient synthesis of (±)-tropan-2-one
Lomenzo,Enmon,Troyer,Trudell
, p. 3681 - 3690 (2007/10/03)
The facile and efficient multigram synthesis of (±)-tropan-2-one 1 was achieved in six steps (65% overall yield) from N-methyl-3-oxopyridyl hydroiodide 3.
Solvolytic Rearrangements of Azabicyclic Compounds. Part 2. Kinetics
Bastable, John W.,Dunkin, Ian R.,Hobson, John D.
, p. 1346 - 1351 (2007/10/02)
Rates of solvolysis in aqueous ethanol and aqueous dioxan of three 2-exo-chloroazabicycloalkanes have been studied and first-order rare constants are derived and compared with published values for analogous compounds.Anchimeric assistance by the bridge N-atom is evidently not important in the rate-controlling step in these rearrangements, though it may occur to a minor extent in the case of 2-exo-chloro-7-methyl-7-azanorbornane.Solvolytic results for tropan-2β-yl toluene-p-sulphonate in aqueous ethanol and aqueous acetone mixtures are also reported and compared with literature data for the carbobicyclic and oxabicyclic analogues.
