25290-13-5Relevant academic research and scientific papers
Cyclic Ether Synthesis via Palladium-Catalyzed Directed Dehydrogenative Annulation at Unactivated Terminal Positions
Thompson, Samuel J.,Thach, Danny Q.,Dong, Guangbin
supporting information, p. 11586 - 11589 (2015/09/28)
Here, a palladium-catalyzed functionalization of unactivated sp3 C-H bonds with internal alcohol nucleophiles is described. Directed by an oxime-masked alcohol, annulation chemoselectively occurs at the β position, leading to a range of aliphatic cyclic ethers with four- to seven-membered rings. Tethered primary, secondary, and tertiary free hydroxyl groups can all react to give the corresponding cyclized products. In addition, benzyl and silyl protected alcohols can also be directly coupled. An sp3 C-H activation/intramolecular SN2 pathway was proposed.
Catalyst-controlled wacker-type oxidation of homoallylic alcohols in the absence of protecting groups
McCombs, Jessica R.,Michel, Brian W.,Sigman, Matthew S.
experimental part, p. 3609 - 3613 (2011/06/23)
Homoallylic alcohols are oxidized to β-hydroxy ketones using a TBHP-mediated Pd-catalyzed Wacker-type oxidation. The use of a bidentate ligand, quinoline-2-oxazoline (Quinox), and TBHP(aq) as the terminal oxidant provides good yields of the des
The boron-mediated ketone-ketone aldol reaction
Cergol, Katie M.,Turner, Peter,Coster, Mark J.
, p. 1505 - 1509 (2007/10/03)
The first examples of the directed, boron-mediated aldol reaction between different ketones are presented. Transformation of a variety of ketones to their corresponding boron enolates with Chx2BCl/Et3N, followed by reaction with acceptor ketones in diethyl ether, and oxidation of the resultant boron aldolate (H2O2, MeOH/pH 7 buffer), provided the aldol addition products. The reaction was most facile when cyclic ketones were used, with the highest yields obtained for the reaction of boron enolates with cyclohexanone as the acceptor.
