66948-16-1

Upstream product

• 1721-93-3 1-methylisoquinoline 
• 100-52-7 benzaldehyde 
• 27104-72-9 methyl isoquinoline-1-carboxylate 
• 486-73-7 1-isoquinolinecarboxylic acid 
• 27311-63-3 1-Hydroxymethyl-isoquinoline 
• 27039-28-7 1-(acetoxymethyl)-isoquinoline 

Downstream Products

• 1126532-65-7 (S)-2-(isoquinolin-1-yl)-1-phenylethanol 
• 1126532-47-5 (^SiR,R)-1-[2-(1-tert-butyl-1-silatetralinyl-1-oxy)-2-phenylethyl]isoquinoline 
• 1007107-28-9 (R)-2-isoquinolin-1-yl-1-phenylethanol 
• 1227475-50-4 (S)-1-(2-(bis(3,5-dimethylphenyl)(methyl)silyloxy)-2-phenylethyl)isoquinoline 
• 1007107-20-1 C₃₀H₃₃NOSi 

Relevant academic research and scientific papers

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.

Samarium-promoted coupling of pyridine-based heteroaryl analogues of benzylic acetates with carbonyl compounds

(Chemical Equation Presented) 2-Substituted pyridine, quinoline, isoquinoline, bipyridine, and 1,10-phenanthroline analogues of benzylic acetates undergo Sml2-promoted coupling with aldehydes and ketones to afford (2-hydroxyalkyl)heteroaromatics.

AN ALDOL-TYPE REACTION OF ACTIVE METHYL GROUPS OF NITROGEN-CONTAINING HETEROAROMATIC COMPOUNDS

Active methyl groups of nitrogen-containing heteroaromatic compounds react with benzaldehydes in the presence of 9-BBN triflate and diisopropylethylamine in dichloromethane to give the corresponding aldol-type products under mild conditions.

LATERAL METALLATION OF METHYLATED NITROGENOUS HETEROCYCLES

Me groups on nitrogenous heterocycles can be conveniently metallated by a variety of strongly basic reagents to afford synthetically useful carbanions.The negative charge of such anions resides predominantly on the ring N atoms.The site of lithiation on pyridines and quinolines bearing Me groups in both the 2- and 4-positions depends upon the ability of the ring N atom to complex with the metallating agents.Carbanions derived from methylated pyridines, quinolines, naphthyridines, isoquinolines, pyridocarbazoles, pteridines, pyridoindoles and quinoxalines are discussed.References are provided describing condensations of these reagents with a variety of both common and uncommon electrophiles.