1126532-64-6

Upstream product

• 851542-50-2 (SiR)-1-tert-butyl-1,2,3,4-tetrahydro-1-silanaphthalene 
• 38101-94-9 rac-1-phenyl-2-(quinolin-2-yl)ethanol 
• 5796-80-5 1-phenyl-2-(quinolin-2(1H)-ylidene)ethanone 
• 1696-17-9 N,N-diethylbenzamide 
• 91-63-4 2-methylquinoline 
• 919513-39-6 (SiS)-1-tert-butyl-1,2,3,4-tetrahydro-1-silanaphthalene 

Relevant academic research and scientific papers

Highly efficient asymmetric bioreduction of 1-aryl-2-(azaaryl)ethanones. Chemoenzymatic synthesis of lanicemine

Different ketoreductases (KREDs) have been used to promote a highly selective reduction of several 1-aryl-2-(azaaryl)ethanones (azaaryl = pyridinyl, quinolin-2-yl), the corresponding secondary alcohols being obtained with very high yields and enantiomeric excesses (ee > 99%). The absolute configuration of each optically active alcohol has been assigned by means of modified Mosher and Kelly methods, two shielding effects being evaluated: (1) the Mosher phenyl ring effect on the azaaryl protons and (2) the one of the azaaryl ring on the Mosher methoxy group. In addition, the biologically active amine lanicemine has been synthesized from (R)-1-phenyl-2-(pyridin-2-yl)ethanol, thus proving the utility of the secondary alcohols here prepared.

Stereoselective alcohol silylation by dehydrogenative Si-O coupling: Scope, limitations, and mechanism of the Cu-H-catalyzed non-enzymatic kinetic resolution with silicon-stereogenic silanes

Ligand-stabilized copper(I)hydride catalyzes the dehydrogenative Si-O coupling of alcohols and silanes-a process that was found to proceed without racemization at the silicon atom if asymmetrically substituted. The present investigation starts from this pivotal observation since silicon-stereogenic silanes are thereby suitable for the reagent-controlled kinetic resolution of racemic alcohols, in which asymmetry at the silicon atom enables discrimination of enantiomeric alcohols. In this full account, we summarizeour efforts to systematically examine this unusual strategy of diastereoselective alcohol silylation. Ligand (sufficient reactivity with moderately electron-rich monophosphines), silane (reasonable diastereocontrol with cyclic silanes having a distinct substitution pattern) as well as substrate identification (chelating donor as a requirement) areintroductorily described. With these basic data at hand, the substrate scope was defined employing enantiomerically enriched tert-butyl-substituted 1-silatetraline and highly reactive 1-si-laindane. The synthetic part is complemented by the determination of the stereochemical course at the silicon atom in the Si-O coupling step followed by its quantum-chemical analysis thus providing a solid mechanistic picture of this remarkable transformation.

Chiral recognition with silicon-stereogenic silanes: Remarkable selectivity factors in the kinetic resolution of donor-functionalized alcohols

(Chemical Equation Presented) Slick silicon: A low-molecular-weight silane (C13H20Si, 204.38 g mol-1) with silicon-centered chirality is capable of discriminating enantiomeric rhodium-substrate complexes in dehydrogenative Si-O coupling reactions with outstanding selectivity factors (see scheme, s = selectivity factor).