949568-50-7

Upstream product

• 60691-90-9 3-bromo-1-(p-chlorophenyl)-1-propene 
• 100-58-3 phenylmagnesium bromide 
• 591-51-5 phenyllithium 
• 104-88-1 4-chlorobenzaldehyde 
• 682339-15-7 phosphoric acid 3-(4-chlorophenyl)allyl ester diethyl ester 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 

Relevant academic research and scientific papers

Chiral Diarylmethanes via Copper-Catalyzed Asymmetric Allylic Arylation with Organolithium Compounds

A highly enantioselective copper/N-heterocyclic carbene catalyzed allylic arylation with organolithium compounds is presented. The use of commercial or readily prepared aryllithium reagents in the reaction with allyl bromides affords a variety of chiral diarylvinylmethanes, comprising a privileged structural motif in pharmaceuticals, in high yields with good to excellent regio- and enantioselectivities. The versatility of this new transformation is illustrated in the formal synthesis of the marketed drug tolterodine (Detrol).

Catalytic asymmetric carbong-carbon bond formation via allylic alkylations with organolithium compounds

Carbon-carbon bond formation is the basis for the biogenesis of nature's essential molecules. Consequently, it lies at the heart of the chemical sciences. Chiral catalysts have been developed for asymmetric C-C bond formation to yield single enantiomers from several organometallic reagents. Remarkably, for extremely reactive organolithium compounds, which are among the most broadly used reagents in chemical synthesis, a general catalytic methodology for enantioselective C-C formation has proven elusive, until now. Here, we report a copper-based chiral catalytic system that allows carbon-carbon bond formation via allylic alkylation with alkyllithium reagents, with extremely high enantioselectivities and able to tolerate several functional groups. We have found that both the solvent used and the structure of the active chiral catalyst are the most critical factors in achieving successful asymmetric catalysis with alkyllithium reagents. The active form of the chiral catalyst has been identified through spectroscopic studies as a diphosphine copper monoalkyl species.

Copper-catalyzed asymmetric allylic substitution of allyl phosphates with aryl- and alkenylboronates

The asymmetric allylic substitution of allyl phosphates with aryl- and alkenylboronates catalyzed by a copper/N-heterocyclic carbene complex was developed and the substitution products were obtained with high enantioselectivity (see scheme). To account for the observed influence of the reaction parameters a possible catalytic cycle for this process was proposed. Copyright

Efficient chiral N-heterocyclic carbene/copper(I)-catalyzed asymmetric allylic arylation with aryl Grignard reagents

Gamma rules: The title reaction was achieved in a highly regioselective manner using aryl Grignard reagents with monodentate chiral N-heterocyclic carbenel copper(I) catalyst to givediarylvinylmethanes with excellent enantiomeric excess in excellent yield

Copper-catalyzed asymmetric allylic substitution with aryl and ethyl Grignard reagents

Phenyl- and ethyl-magnesium bromides undergo regioselective asymmetric allylic substitution with high enantioselectivity under the catalysis of chiral amidophosphane-copper(i) complexes. The Royal Society of Chemistry.