105364-41-8Relevant academic research and scientific papers
Improved synthesis of 2-(4-propylphenyl)ethanol
Hashmi, A. Stephen K.,Burkert, Tobias,Bats, Jan W.,Martyniak, Aleksandra
, p. 179 - 181 (2006)
A new procedure for the synthesis of 2-(4-propylphenyl)ethanol is provided. This new procedure significantly reduces side-products as 1-(4-propylphenyl) ethanol and 2-bromoethanol, which are obtained when using the previously known procedure. Only with the new procedure an efficient purification on the large scale needed for avoided-level-crossing muon-spin resonance experiments was possible. Structural details of the title compound could be derived from an X-ray structure analysis of a crystalline derivative, the nitrobenzoyl ester.
Preparation of highly enantiomerically pure linear secondary alcohols via asymmetric reduction of prochiral ketones with borane
Xu, Jiaxi,Su, Xianbin,Zhang, Qihan
, p. 1781 - 1786 (2003)
An efficient and practical preparation of homochiral linear secondary alcohols, 1-(4-alkylphenyl) and 1-(4-alkoxylphenyl) alcohols, via the asymmetric oxazaborolidine-catalyzed borane reduction of prochiral ketones is described. The phenomenon of the enan
Transformation of Alkynes into Chiral Alcohols via TfOH-Catalyzed Hydration and Ru-Catalyzed Tandem Asymmetric Hydrogenation
Liu, Sensheng,Liu, Huan,Zhou, Haifeng,Liu, Qixing,Lv, Jinliang
, p. 1110 - 1113 (2018/02/23)
A novel full atom-economic process for the transformation of alkynes into chiral alcohols by TfOH-catalyzed hydration coupled with Ru-catalyzed tandem asymmetric hydrogenation in TFE under simple conditions has been developed. A range of chiral alcohols was obtained with broad functional group tolerance, good yields, and excellent stereoselectivities.
One-pot synthesis of chiral alcohols from alkynes by CF3SO3H/ruthenium tandem catalysis
Liu, Huan,Liu, Sensheng,Zhou, Haifeng,Liu, Qixing,Wang, Chunqin
, p. 14829 - 14832 (2018/04/30)
A practical one-pot synthesis of chiral alcohols from readily available alkynes via tandem catalysis by the combination of CF3SO3H and a fluorinated chiral diamine Ru(ii) complex in aqueous CF3CH2OH is described. Very interestingly, the combination of fluorinated catalysts and solvent exhibits a positive fluorine effect on the reactivity and enantioselectivity. A range of chiral alcohols with wide functional group tolerance was obtained in high yield and excellent stereoselectivity under simple and mild conditions.
Regioselective hydration of terminal alkynes catalyzed by a neutral gold(I) complex [(IPr)AuCl] and one-pot synthesis of optically active secondary alcohols from terminal alkynes by the combination of [(IPr)AuCl] and Cp?RhCl[(R, R)-TsDPEN]
Li, Feng,Wang, Nana,Lu, Lei,Zhu, Guangjun
, p. 3538 - 3546 (2015/04/14)
A neutral gold(I) complex [(IPr)AuCl] (IPr = 1,3-bis(diisopropylphenyl)imidazol-2-ylidene) was found to be a highly effective catalyst for the hydration of terminal alkynes, including aromatic alkynes and aliphatic alkynes. The desired methyl ketones were obtained in high yields with complete regioselectivities. Furthermore, a series of optically active secondary alcohols could be obtained in high yield with good to excellent enatioselectivities via one-pot sequential hydration/asymmetric transfer hydrogenation (ATH) from terminal alkynes by the combination of of [(IPr)AuCl] and Cp?RhCl[(R,R)-TsDPEN] (Cp? = pentamethylcyclopentadienyl, TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine). Notably, this research exhibited the potential of the direct use of neutral gold(I) complexes instead of cationic ones as catalysts for the activation of multiple bonds for organic synthesis.
Two-component supramolecular helical architectures: Creation of tunable dissymmetric cavities for the inclusion and chiral recognition of the third components
Kodama, Koichi,Kobayashi, Yuka,Saigo, Kazuhiko
, p. 2144 - 2152 (2008/02/04)
The inclusion and chiral recognition of racemic arylalkanols by supramolecular helical architectures consisting of enantiopure primary amines and achiral carboxylic acids were thoroughly studied. Among the architectures examined, a supramolecular helical architecture composed of the salt of enantiopure erythro-2-amino-1.2-diphenylethanol (1b) and benzoic acid (2a) was found to include a wide variety of racemic arylalkanols with recognition of their chirality. The helical architecture gave a dissymmetric 1D groove in the salt crystal, and the arylalkanols were enantioselectively included in the groove. The size and shape of the groove were tunable by proper selection of the achiral carboxylic acid component. The origin of the chiral recognition with the combination 1b/2a is discussed on the basis of X-ray crystallographic analyses.
Combined ruthenium(II) and lipase catalysis for efficient dynamic kinetic resolution of secondary alcohols. Insight into the racemization mechanism
Martin-Matute, Belen,Edin, Michaela,Bogar, Krisztian,Kaynak, F. Betuel,Baeckvall, Jan-E.
, p. 8817 - 8825 (2007/10/03)
Pentaphenylcyclopentadienyl ruthenium complexes (3) are excellent catalysts for the racemization of secondary alcohols at ambient temperature. The combination of this process with enzymatic resolution of the alcohols results in a highly efficient synthesis of enantiomerically pure acetates at room temperature with short reaction times for most substrates. This new reaction was applied to a wide range of functionalized alcohols including heteroaromatic alcohols, and for many of the latter, enantiopure acetates were efficiently prepared for the first time via dynamic kinetic resolution (DKR). Different substituted cyclopentadienyl ruthenium complexes were prepared and studied as catalysts for racemization of alcohols. Pentaaryl-substituted cyclopentadienyl complexes were found to be highly efficient catalysts for the racemization. Substitution of one of the aryl groups by an alkyl group considerably slows down the racemization process. A study of the racemization of (S)-1-phenylethanol catalyzed by ruthenium hydride η5-Ph5CpRu(CO) 2H (8) indicates that the racemization takes place within the coordination sphere of the ruthenium catalyst. This conclusion was supported by the lack of ketone exchange in the racemization of (S)-1-phenylethanol performed in the presence of p-tolyl methyl ketone (1 equiv), which gave 1% of 1-(p-tolyl)ethanol. The structures of ruthenium chloride and iodide complexes 3a and 3c and of ruthenium hydride complex 8 were confirmed by X-ray analysis.
ASYMMETRIC REDUCTION OF p-ALKYLACETOPHENONES
Cervinka, Otakar,Fabryova, Anna,Brozova, Ivana,Holik, Miroslav
, p. 684 - 686 (2007/10/02)
Asymmetric reduction of p-alkylacetophenones Ia-VIIa with lithium aluminium hydride in the presence of (-)-quinine affords optically active alcohols Ib-VIIb of the (R)-(+) configuration in optical yields about 50 percent.
