1001158-63-9

Upstream product

• 98-86-2 acetophenone 
• 1398647-62-5 5,5-dimethyl-2-(2-methylallyl)-1,3,2-dioxaborinane 
• 90-82-4 pseudoephedrine 
• 1458-98-6 2-methyl-3-bromo-1-propene 

Relevant academic research and scientific papers

Design and synthesis of modular oxazoline ligands for the enantioselective chromium-catalyzed addition of allyl bromide to ketones

By systematically evaluating ligand diastereomers using a modular oxazoline template, a new ligand has been identified leading to the discovery of the first example of a chromium-catalyzed enantioselective allylation of ketones using allylic bromides. Cop

Asymmetric methallylation of ketones catalyzed by a highly active organocatalyst 3,3′-F2-BINOL

(S)-3,3′-F2-BINOL has been synthesized for the first time and demonstrated as a highly active organocatalyst for asymmetric methallylation of ketones. Up to 98:2 enantioselectivity and 99% yield were obtained with 5 mol % catalyst loading. The

Direct synthesis of B-allyl and B-allenyldiisopinocampheylborane reagents using allyl or propargyl halides and indium metal under Barbier-type conditions

We report the first one-pot process for the asymmetric addition of allyl, methallyl, and propargyl groups to aldehydes and ketones using B-chlorodiisopinocampheylborane (dDIP-Cl) and indium metal. Under Barbier-type conditions, indium metal was

Indium-mediated asymmetric Barbier-type allylations: Additions to aldehydes and ketones and mechanistic investigation of the organoindium reagents

(Chemical Equation Presented) We report a simple, efficient, and general method for the indium-mediated enantioselective allylation of aromatic and aliphatic aldehydes and ketones under Barbier-type conditions in a one-pot synthesis affording the corresponding chiral alcohol products in very good yield (up to 99%) and enantiomeric excess (up to 93%). Our method is able to tolerate various functional groups, such as esters, nitriles, and phenols. Additionally, more substituted allyl bromides, such as crotyl and cinnamyl bromide, can be used providing moderate enantioselectivity (72% and 56%, respectively) and excellent diastereoselectivity when employing cinnamyl bromide (95/5 anti/syn). However, the distereoselectivity when using crotyl bromide was poor and other functionalized allyl bromides under our method afforded low enantioselectivities for the alcohol products. In these types of indium-mediated additions, solvent plays a major role in determining the nature of the organoindium intermediate and we observed the susceptibility of some allylindium intermediates to hydrolysis in protic solvents. Under our reaction conditions using a polar aprotic solvent, we suggest that an allylindium(III) species is the active allylating intermediate. In addition, we have observed the presence of a shiny, indium(0) nugget throughout the reaction, irrespective of the stoichiometry, indicating disproportionation of indium halide byproduct formed during the reaction.

Asymmetric synthesis of 2°- and 3°-carbinols via B-methallyl-10-(TMS and Ph)-9-borabicyclo[3.3.2]decanes

(Chemical Equation Presented) Simple Grignard procedures provide methallylboranes 1a and 1b in enantiomerically pure form from air-stable precursors in 98% and 95% yields, respectively. These reagents add smoothly to aldehydes and methyl ketones, respecti