611-69-8Relevant articles and documents
Catalytic asymmetric transfer hydrogenation of ketones using terpene-based chiral β-amino alcohols
Watts, Cian Christopher,Thoniyot, Praveen,Cappuccio, Frank,Verhagen, Joelle,Gallagher, Brain,Singaram, Bakthan
, p. 1301 - 1307 (2006)
Catalytic asymmetric transfer hydrogenations of aromatic alkyl ketones have been studied using [RuCl2(p-cymeme)]2 and terpene-based β-amino alcohols. The limonene derived amino alcohol, (1S,2S,4R)-1-methyl-4-(1-methylethenyl)-2-(meth
Pinacol versus para coupling of aromatic ketones
Maury, Olivier,Villiers, Claude,Ephritikhine, Michel
, p. 6591 - 6594 (1997)
Aromatic ketones PhCOR were coupled with uranium complexes to give, after deuterolysis, the pinacol 3 and the keto-alcohol 4 resulting respectively from the pinacol and para coupling of the carbonyl substrate. The organometallic precursors of 3 and 4 were
Cyclometalated (NNC)Ru(ii) complex catalyzed β-methylation of alcohols using methanol
Belkova, Natalia V.,Ganguli, Kasturi,Kundu, Sabuj
supporting information, p. 4354 - 4365 (2022/04/07)
Indolyl fragment containing phenanthroline based new ligands and their corresponding Ru(ii) complexes were synthesized and fully characterized by various spectroscopic techniques. The catalytic activity of these newly synthesized cyclometalated (NNC)Ru(ii) complexes was explored towards the β-methylation of alcohols using methanol. Notably, these complexes displayed superior reactivity compared to various (NNN)Ru(ii) complexes. Utilizing this strategy, a wide range of primary, secondary, and aliphatic straight chain alcohols were selectively methylated. This protocol was further employed for the methylation of a few natural products and the gram scale synthesis of β-methylated alcohols. A series of control experiments and kinetic studies were performed to understand the plausible reaction mechanism.
Highly efficient NHC-iridium-catalyzed β-methylation of alcohols with methanol at low catalyst loadings
Lu, Zeye,Zheng, Qingshu,Zeng, Guangkuo,Kuang, Yunyan,Clark, James H.,Tu, Tao
, p. 1361 - 1366 (2021/06/30)
The methylation of alcohols is of great importance since a broad number of bioactive and pharmaceutical alcohols contain methyl groups. Here, a highly efficient β-methylation of primary and secondary alcohols with methanol has been achieved by using bis-N-heterocyclic carbene iridium (bis-NHC-Ir) complexes. Broad substrate scope and up to quantitative yields were achieved at low catalyst loadings with only hydrogen and water as by-products. The protocol was readily extended to the β-alkylation of alcohols with several primary alcohols. Control experiments, along with DFT calculations and crystallographic studies, revealed that the ligand effect is critical to their excellent catalytic performance, shedding light on more challenging Guerbet reactions with simple alcohols. [Figure not available: see fulltext.].
Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts
Oestreich, Martin,Seliger, Jan
supporting information, p. 247 - 251 (2020/10/29)
A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition-metal-catalyzed alcohol racemization and enantioselective Cu-H-catalyzed dehydrogenative Si-O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization of the silyl ether and its unselective formation. Often-used ruthenium half-sandwich complexes are not suitable but a bifunctional ruthenium pincer complex perfectly fulfills this purpose. By this, enantioselective silylation of racemic alcohol mixtures is achieved in high yields and with good levels of enantioselection.