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 
• 75851-76-2 1-phenylpent-3-en-1-ol 
• 294675-19-7 2,2-dimethyl-hept-5-en-3-ol 
• 136106-47-3 (E)-Tridec-2-en-5-ol 
• 294675-18-6 1-cyclohexyl-pent-3-en-1-ol 
• 504-61-0 (E)-but-2-enol 
• 598-32-3 2-hydroxy-3-butene 
• 18147-55-2 (Z)-crotyltrichlorosilane 
• 106-99-0 buta-1,3-diene 

Downstream Products

• 169827-08-1 (S,Z)-1-phenylhept-5-en-3-ol 
• 169827-07-0 (E)-1-phenyl-hept-5-en-3-ol 
• 138298-43-8 (3S)-1-phenylheptan-3-ol 
• 369651-19-4 (3R,5E)-1-phenyl-5-heptene-3-ol 
• 261917-84-4 (3S,5Z)-1-phenyl-5-heptene-3-ol 
• 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 

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.

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.

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

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

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.

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

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.

Electrophile-induced ether transfer: A new approach to polyketide structural units

A strategically novel approach to the formation of syn-1,3-diol mono- and diethers through electrophilic activation of homoallylic alkoxymethyl ethers has been developed. The resulting polyketide-like synthetic fragments are generated in good yield and wi

Cr-waste free catalytic carbonyl addition reactions with polymer-immobilized CrF2

A monomeric [Cr(pyridine)4F2]+Br- is immobilized onto the dipyridyl-TentaGel resin. Allylations of aldehydes with 5-10 mol % of the CrF2-dipyridyl-TentaGel resin 2/Mn/TMSCl in THF provide the correspo