30314-63-7Relevant academic research and scientific papers
Chiral 2-(2-hydroxyaryl)alcohols (HAROLs) with a 1,4-diol scaffold as a new family of ligands and organocatalysts
Dilek, ?mer,Tezeren, Mustafa A.,Tilki, Tahir,Ertürk, Erkan
supporting information, p. 268 - 286 (2017/12/06)
Efficient and modular syntheses of chiral 2-(2-hydroxyaryl)alcohols (HAROLs), novel 1,4-diols carrying one phenolic and one alcohol hydroxyl group, have been developed which led to generation of a small library of structurally diverse HAROLs in enantiomerically pure form. Of the different HAROLs examined, a HAROL based on the indan backbone exhibited the highest activity and enantioselectivity in the 1,2-addition of certain organometallic compounds to aldehydes in the presence of Ti(OiPr)4 (up to 97% y, 88% ee) and performed as a hydrogen-bond donor organocatalyst in the Morita-Baylis-Hillman reaction, promoted by trialkylphosphines.
Regioselective ring-opening of epoxides with ortho-lithioanisoles catalyzed by BF3·OEt2
Ertürk, Erkan,Tezeren, Mustafa A.,Atalar, Taner,Tilki, Tahir
experimental part, p. 6463 - 6471 (2012/08/27)
It is presented that a number of o-2-hydroxyalkylanisoles could be efficiently synthesized through the regioselective ring-opening reaction of epoxides with o-lithioanisoles in the presence of BF3·OEt 2 Lewis-acid catalyst. Sterically demanding o-lithioanisoles had to be generated by exploiting the combination of nBuLi and a catalytic amount of TMEDA (0.20 equiv) in Et2O as the lithiator whereas 'normal' anisole could be lithiated at ortho-position by treatment with nBuLi in THF as usual. Surprisingly, the availability of THF and a catalytic amount of TMEDA (0.20 equiv) in the reaction mixture was found to enhance the reaction yields dramatically. A complex aggregate formation by the co-operative ligation of THF and TMEDA to ortho-lithioanisole(s) was proposed to rationalize the high reactivity achieved in the ring-opening reaction of epoxides.
1,2-Diarylethanols by alternative regioselective reductive ring-opening of 2,3-diaryloxiranes
Blasio, Nadia Di,Lopardo, Maria Teresa,Lupattelli, Paolo
supporting information; experimental part, p. 938 - 944 (2009/07/19)
Non-symmetrical ￡rans-2,3-diaryloxiranes have been regioselectively opened by catalytic hydrogenation over Pd/C, NaBH4/Pd and [Cp 2TiCl]/H2O. Although in the catalytic hydrogenation reactions the epoxides were mainly opened at the β-carbon with respect to the substituted aryl ring in all cases, with the [Cp2TiCl]/H 2O system the regioselectivity was affected by the electronic properties of the aryl residues, the epoxides being opened on the carbon bearing the most electron-releasing or the least electron-withdrawing group. With the NaBH4/Pd system different regioisomers were obtained depending on the substituents. Starting from enantioenriched epoxides, no loss of optical purity was observed in the alcohols formed.
Functionalized benzylic magnesium reagents through a sulfur-magnesium exchange
Stoll, Armin H.,Krasovskiy, Arkady,Knochel, Paul
, p. 606 - 609 (2007/10/03)
(Chemical Equation Presented) Switch it: lodobiphenyl thioethers readily undergo an iodine-magnesium exchange followed by, after the addition of tBuOLi, an intramolecular sulfur-magnesium exchange, which provides benzylic magnesium reagents in excellent yield through a fragmentation reaction.
