119582-57-9Relevant 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
, p. 11586 - 11589 (2015)
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.
Regiocontrol synthesis of β-trimetylsilyloxy carbonyl compounds through an aldolgrignard elaboration sequence
Palomo, Caludio,Aizpurua, Jesus M.,Aurrejoetxea, Natalia,Lopez, M. Conception
, p. 2525 - 2528 (2007/10/02)
Reaction of carbonyl compounds with α-lithio- or α-halozinc N-methoxy-N-methylamides, followed by silylation and Grignard addition resulted in a regiocontrolled synthesis of β-trimethylsilyloxy carbonyl compounds.
Crossed aldol-type reactions catalyzed by rhodium complexes
Sato, Susumu,Matsuda, Isamu,Izumi, Yusuke
, p. 223 - 238 (2007/10/02)
Crossed aldol-type reactions of enol trimethylsilyl ethers with aldehydes and ketones are smooth when carried out with a catalytic amount of a rhodium complex, Rh4(CO)12 or X (X=PF6 and ClO4; COD=cycloocta-1,5-diene, DPPB=1,4-bis(diphenylphosphino)butane), under neutral conditions.A suitable catalyst enables the isolation of three different types of aldol reaction product, β-trimethylsiloxy ketones, β-hydroxy ketones, and α,β-unsaturated ketones.Rh4(CO)12 and ClO4 also catalyze the reaction of enol trimethylsilyl ethers with acetals or ketals, whereas PF6 does not.When ClO4 is used as the catalyst, this type of aldol reaction is extended to the one-pot synthesis of trisubstituted furans from enol trimethylsilyl ether and α-trimethylsiloxy acetal.
