76156-40-6Relevant academic research and scientific papers
Highly regioselective copper-catalyzed cis- and trans-1-propenyl Grignard cleavage of hindered epoxides. Application in propionate synthesis
Rodriguez, David,Mulero, Marlenne,Prieto, Jose A.
, p. 5826 - 5829 (2006)
Hindered protected and unprotected epoxy alcohols were regioselectively cleaved using copper-catalyzed cis- and trans-1-propenylmagnesium bromide. The reaction exhibited good yield and excellent regioselectivity in systems where organocuprates and organoalanes failed. The cis Grignard reagent displayed no double-bond isomerization, whereas the trans isomer showed partial trans-to-cis equilibration, which was minimized by controlling the reagent formation conditions. The reaction was shown to be highly useful for the elaboration of the C10-C15 Streptovaricin D ansa chain fragment.
Alkylaluminum Halide Induced Cyclization of Unsaturated Carbonyl Compounds
Snider, Barry B.,Karras, Michael,Price, Robert T.,Rodini, David J.
, p. 4538 - 4545 (2007/10/02)
2,6-Dimethyl-5-heptenal (3) and 5-octenal (24) undergo concerted ene reactions with 1 equiv of Me2AlCl and cation-olefin cyclizations with 2 equiv of Me2AlCl, MeAlCl2, or EtAlCl2 to give a zwitterion which reacts to give several products including an ene
