329796-89-6

Upstream product

• 1571-08-0 methyl 4-formylbenzoate 
• 1730-25-2 allylmagnesium bromide 
• 106-95-6 allyl bromide 
• 124-41-4 sodium methylate 
• 85116-38-7 (+)-diisopinocampheylallylborane 
• 619-66-9 4-Carboxybenzaldehyde 
• 124821-92-7 d-B-allylbis(2-isocaranyl)borane 
• 99493-25-1 diisopropyl (R,R)-2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate 
• 591-87-7 Allyl acetate 
• 6908-41-4 4-(methoxycarbonyl)benzyl alcohol 
• 369651-27-4 (1S,2S,5R)-1-allyl-2-isopropyl-5-methylcyclohexanol 

Downstream Products

• 329796-97-6 4-((S)-1-Hydroxy-but-3-enyl)-benzoic acid 
• 915105-89-4 C₁₁H₁₂⁽²⁾H₂O₂ 
• 935559-76-5 4-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-benzoic acid methyl ester 
• 935559-78-7 (S)-1-(4-benzyloxymethyl-phenyl)-but-3-en-1-ol 
• 935559-77-6 {4-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-phenyl}-methanol 
• 915105-92-9 C₂₁H₃₂⁽²⁾H₂O₄Si 
• 915105-91-8 C₁₉H₂₈⁽²⁾H₂O₃Si 
• 915105-90-7 C₁₇H₂₆⁽²⁾H₂O₂Si 
• 915105-93-0 C₁₅H₁₇⁽²⁾HO₄ 

Relevant academic research and scientific papers

Heteropoly Acid Supported on Silica Gel as Catalyst for the Asymmetric Transfer Allylation of Aromatic Aldehydes under Solvent-Free Conditions

A new convenient method for the asymmetric transfer allylation of aromatic aldehydes was developed. The reaction gave the best results using a chiral allyl donor molecule derived from (-)-menthone in the presence of heteropoly acids supported on silica gel under solvent-free conditions, and the desired homoallylic alcohol derivatives were obtained in good yields with good to high enantioselectivity.

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.

Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level using allyl acetate as an allyl metal surrogate

Protocols for highly enantioselective carbonyl allylation from the alcohol or aldehyde oxidation level are described based upon transfer hydrogenative C-C coupling. Exposure of allyl acetate to benzylic alcohols 1a-i in the presence of an iridium catalyst derived from [IrCl(cod)]2 and (R)-BINAP delivers products of C-allylation 2a-i. Employing isopropanol as terminal reductant, exposure of allyl acetate to aryl aldehydes 3a-i in the presence of an iridium catalyst derived from [IrCl(cod)]2 and (-)-TMBTP delivers identical products of C-allylation 2a-i. In all cases examined, exception levels of enantioselectivity are observed. Thus, enantioselective carbonyl allylation is achieved from the alcohol or aldehyde oxidation level in the absence of any preformed allylmetal reagents. These studies define a departure from preformed organometallic reagents in carbonyl additions that transcend the boundaries of oxidation level. Copyright

Competitive cationic pathways and the asymmetric synthesis of aryl-substituted cyclopropanes

Equation presented 1,2-Disubstituted cyclopropanes were synthesized in a nonracemic fashion via activation of the corresponding homoallylic alcohols in excellent yields. A series of substituted phenyl rings showed higher enantiospecificity for the cyclization as the electron-withdrawing ability of the group increased. The results offer strong support for the existence of competing cation mechanisms.

Stereoselective allylation of aldehydes on solid support and its application in biology-oriented synthesis (BIOS)

A systematic study on the asymmetric allylation of aldehydes on solid support is reported. Different kinds of chiral allylboron reagents with complementary direction of stereoinduction were applied successfully in this reagent-controlled transformation. T

Indium-mediated Barbier-type allylation of aldehydes as a convenient method for the highly enantioselective synthesis of homoallylic alcohols

We report a general method for the indium-mediated Barbier-type enantioselective allylation of both aromatic and aliphatic aldehydes using commercially available (1S,2R)-(+)-2-amino-1,2-diphenylethanol as a chiral auxiliary. Using only two equivalents of allyl bromide, excellent yields and very good to excellent enantioselectivities are obtained. To our knowledge, the enantioselectivities reported herein are the highest obtained for indium-promoted allylations of carbonyl compounds.

A synthetic library of cell-permeable molecules

Small molecules that induce or stabilize the association of macromolecules have proven to be useful effectors of a wide variety of biological processes. To date, all examples of such chemical inducers of dimerization have involved known ligands to well-ch