304459-85-6

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 4784-77-4 (E/Z)-crotyl bromide 
• 95-14-7 1,2,3-Benzotriazole 
• 69611-01-4 (Z)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 69611-02-5 (E)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 504-61-0 (E)-but-2-enol 
• 598-32-3 2-hydroxy-3-butene 
• 18147-55-2 (Z)-crotyltrichlorosilane 
• 61967-12-2 2-methyl-1,1-diphenylbut-3-en-1-ol 
• 66534-32-5 α,α-diisopropyl-β-methylhomoallylic alcohol 
• 106-99-0 buta-1,3-diene 
• 294675-18-6 1-cyclohexyl-pent-3-en-1-ol 
• 136106-47-3 (E)-Tridec-2-en-5-ol 

Downstream Products

• 1264758-30-6 5-[2,5-dimethyl-6-(2-phenethyl)pyridin-3-yl]-1H-indole 
• 1264758-14-6 5-methyl-8-phenyloct-3-ene-2,6-dione 
• 1264758-13-5 5-methyl-8-phenyloct-4-ene-2,6-dione 
• 1264758-15-7 3,6-dimethyl-2-phenethylpyridine 
• 369651-19-4 (3R,5E)-1-phenyl-5-heptene-3-ol 
• 261917-84-4 (3S,5Z)-1-phenyl-5-heptene-3-ol 
• 138298-43-8 (3S)-1-phenylheptan-3-ol 
• 169827-07-0 (E)-1-phenyl-hept-5-en-3-ol 
• 169827-08-1 (S,Z)-1-phenylhept-5-en-3-ol 

Relevant academic research and scientific papers

Chiral-anion-dependent inversion of diastereo- and enantioselectivity in carbonyl crotylation via ruthenium-catalyzed butadiene hydrohydroxyalkylation

The ruthenium catalyst generated in situ from H2Ru(CO)(PPh 3)3, (S)-SEGPHOS, and a TADDOL-derived phosphoric acid promotes butadiene hydrohydroxyalkylation to form enantiomerically enriched products. Notably, the observed diastereo- and enantioselectivity is the opposite of that observed using BINOL-derived phosphate counterions in combination with (S)-SEGPHOS, the same enantiomer of the chiral ligand. Match/mismatch effects between the chiral ligand and the chiral TADDOL-phosphate counterion are described. For the first time, single-crystal X-ray diffraction data for a ruthenium complex modified by a chiral phosphate counterion are reported.

Chiral zinc-catalyzed asymmetric α-alkylallylation and α-chloroallylation of aldehydes

Two birds with one stone: In the presence of Zn(OH)2 and a chiral bipyridine ligand, racemic α-substituted allylboronates 2 reacted with aldehydes 1 (see scheme) exclusively in an α-addition fashion to afford various homoallylic alcohols 3 bear

Enhanced anti-diastereo- and enantioselectivity in alcohol-mediated carbonyl crotylation using an isolable single component iridium catalyst

The cyclometalated iridium complex (S)-I derived from [Ir(cod)Cl] 2, 4-cyano-3-nitrobenzoic acid, allyl acetate, and (S)-SEGPHOS is conveniently isolated by precipitation or through conventional silica gel flash chromatography. This single-component precatalyst allows alcohol mediated carbonyl crotylations to be performed at significantly lower temperature, resulting in enhanced levels of anti-diastereo- and enantioselectivity. Most significantly, the chromatographically isolated precatalyst (S)-I enables carbonyl crotylations that are not possible under previously reported conditions involving in situ generation of (S)-I.

Heteroaromatic synthesis via olefin cross-metathesis: Entry to polysubstituted pyridines

The olefin cross-metathesis reaction provides a rapid and efficient method for the synthesis of α,β-unsaturated 1,5-dicarbonyl derivatives which then serve as effective precursors to mono-tetrasubstituted pyridines. Manipulation of the key 1,5-dicarbonyl intermediate allows access to pyridines with a wide range of substitution patterns. An extension of this methodology facilitates the preparation of pyridines embedded within macrocycles, as exemplified by an efficient synthesis of (R)-(+)-muscopyridine. High levels of regiocontrol, short reaction sequences, and facile substituent variation are all notable aspects of this methodology.(Figure Presented)

Anti-diastereo-and enantioselective carbonyl crotylation from the alcohol or aldehyde oxidation level employing a cyclometallated iridium catalyst: α-methyl allyl acetate as a surrogate to preformed crotylmetal reagents

Under the conditions of transfer hydrogenation employing an ortho-cyclometallated iridium catalyst generated in situ from [Ir(cod)Cl] 2, 4-cyano-3-nitrobenzoic acid and the chiral phosphine ligand (S)-SEGPHOS, α-methyl allyl acetate couples to

Aqueous Barbier allylation of aldehydes mediated by tin

The aqueous tin-mediated Barbier reaction affords good to excellent yields and moderate syn diastereoselectivity under basic and acidic conditions. The high yields and stereoselectivity observed in the case of o-substituted aldehydes suggest a cyclic orga

Gallium-mediated allyl transfer from bulky homoallyl alcohol to aldehydes or alkynes: Control of dynamic σ-allylgalliums based on retro-allylation reaction

A new method for the preparation and control of dynamic σ-allylgalliums is disclosed. Upon treatment with a Grignard reagent and gallium trichloride, bulky homoallyl alcohols undergo gallium-mediated retro-allylation reaction to provide σ-allylgallium reagents. The σ-allylgallium reagents generated were applied to carbonyl allylation. The retro-allylation reaction generates (Z)- and (E)-σ-crotylgalliums stereospecifically, starting from erythro- and threo-homoallyl alcohols, respectively. The stereochemically defined crotylgallium reagents effected stereoselective allylation of aldehydes. Allylgallation reaction of alkynes with the allylgallium reagents prepared by retro-allylation is also described.

Generation of allylic indium by hydroindation of 1,3-dienes and one-pot reaction with carbonyl compounds

A hydroindation of 1,3-dienes by dichloroindium hydride (HInCl2) generates allylic indiums that react with carbonyl or imine moieties in a one-pot treatment. The former reaction proceeds in a radical manner, and the latter is ionic allylation.

Chiral phosphoramide-catalyzed enantioselective addition of allylic trichlorosilanes to aldehydes. Preparative studies with bidentate phosphorus-based amides

On the basis of the mechanistic insight that more than one Lewis basic moiety (phosphoramide) is involved in the rate- and stereochemistry-determining step of enantioselective allylation, bidentate chiral phosphoramides were developed. Different chiral phosphoramide moieties were connected by tethers of methylene chains of varying length. The rate and enantioselectivity of allylation with allyltrichlorosilane promoted by the bidentate phosphoramides was found to be highly dependent on the tether length. A new phosphoramide based on a 2,2′-bispyrrolidine skeleton has been designed and afforded good yield, efficient turnover, and high enantioselectivity in allylation reactions. The synthesis of enantiopure 2,2′-bispyrrolidine was easily accomplished on large scale by photodimerization of pyrrolidine followed by resolution with L(or D)-tartaric acid. The scope of the allylation reaction was examined with variously substituted allylic trichlorosilanes and unsaturated aldehydes. This method has been applied to the construction of stereogenic, quaternary centers by the addition of unsymmetrically γ-disubstituted allylic trichlorosilanes.

Dibutyltin oxide catalyzed allyl-transfer reaction from tertiary homoallylic alcohols to aldehydes

A catalytic allyl-transfer reaction from tertiary homoallylic alcohols to aldehydes was achieved using dibutyltin oxide as a catalyst in toluene under reflux conditions. Various secondary homoallylic alcohols were prepared in high yield (up to 99%). When β-alkylated tertiary homoallylic alcohols were used, branched products were exclusively obtained. Georg Thieme Verlag Stuttgart.