5989-27-5Relevant articles and documents
Enantioselective Tail-to-Head Cyclizations Catalyzed by Dual-Hydrogen-Bond Donors
Kutateladze, Dennis A.,Strassfeld, Daniel A.,Jacobsen, Eric N.
, p. 6951 - 6956 (2020/05/19)
Chiral urea derivatives are shown to catalyze enantioselective tail-to-head cyclization reactions of neryl chloride analogues. Experimental data are consistent with a mechanism in which ?-participation by the nucleophilic olefin facilitates chloride ionization and thereby circumvents simple elimination pathways. Kinetic and computational studies support a cooperative mode of catalysis wherein two molecules of the urea catalyst engage the substrate and induce enantioselectivity through selective transition state stabilization.
Upcycling a plastic cup: One-pot synthesis of lactate containing metal organic frameworks from polylactic acid
Slater, Benjamin,Wong, So-On,Duckworth, Andrew,White, Andrew J. P.,Hill, Matthew R.,Ladewig, Bradley P.
supporting information, p. 7319 - 7322 (2019/06/27)
Waste PLA can be upcycled to metal organic frameworks of potential high value in a one-pot synthesis scheme, where PLA depolymerisation occurs in situ. Three homochiral lactate based frameworks were successfully synthesised and characterised from PLA as a feed source, including ZnBLD. The chiral separation ability of ZnBLD was maintained.
Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO2: A Shortcut to (S)-(+)-Lavandulol
Takada, Yuki,Caner, Joaquim,Kaliyamoorthy, Selvam,Naka, Hiroshi,Saito, Susumu
supporting information, p. 18025 - 18032 (2017/12/08)
We report herein a regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to form unsaturated hydrocarbons employing a palladium(II)-loaded titanium oxide; the reaction proceeds at room temperature under light irradiation without stoichiometric generation of salt wastes. Olefin and saturated alcohol moieties tolerated the reaction conditions. Hydrogen atoms were selectively incorporated into less sterically congested carbons of the allylic functionalities. This protocol allowed a short-step synthesis of (S)-(+)-lavandulol from (R)-(?)-carvone by avoiding otherwise necessary protection/deprotection steps.