201854-40-2

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 4784-77-4 (E/Z)-crotyl bromide 
• 95-14-7 1,2,3-Benzotriazole 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 221676-47-7 1-cyclohexyl-2-methyl-but-3-en-1-ol 
• 123186-25-4 1-(2-phenylethyl)-4-penten-1-ol 
• 104-54-1 3-Phenylpropenol 
• 870-63-3 prenyl bromide 
• 598-32-3 2-hydroxy-3-butene 
• 504-61-0 (E)-but-2-enol 
• 90878-19-6 phenethylmagnesium chloride 
• 100-52-7 benzaldehyde 
• 153724-93-7 2-[(E)-3-chloroprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 19781-52-3 2,3-dimethylpent-4-en-2-ol 

Downstream Products

• 147753-18-2 Methyl (E)-5-Hydroxy-7-phenyl-2-heptenoate 
• 1174754-44-9 (E)-1,6-diphenyl-5-hepten-3-ol 

Relevant academic research and scientific papers

Synthesis of cis and trans 2,4,6-tetrahydropyranols via prins-type cyclization and Mitsunob inversion

Prins cyclization of substituted homoallylic alcohol with aryl/aliphatic aldehyde in the presence of a boron trifluoride etherate and trifluoro acetic acid followed by hydrolysis of the resulting trifluoroacetate give substituted cis 2,4,6- tetrahydropyranol products 1-5(c), then Mitsunobu inversion subsequent methanolysis furnished trans 2,4,6-tetrahydropyranol products 1-5(d) stereoselectively in good yield. Our present work reports the synthesis and characterization of these 1-5(c,d) products.

Cp2TiCl2-Catalyzed Photoredox Allylation of Aldehydes with Visible Light

A Barbier-type Cp2TiCl2-mediated (10 mol %) photoredox allylation of aldehydes under irradiation with visible light (blue light-emitting diodes (LEDs), 450 nm) and in the presence of an organic dye (3DPAFIPN, 5 mol %) with allylbromides is described.

Cobalt-Catalyzed Regioselective Olefin Isomerization under Kinetic Control

Olefin isomerization is a significant transformation in organic synthesis, which provides a convenient synthetic route for internal olefins and remote functionalization processes. The selectivity of an olefin isomerization process is often thermodynamically controlled. Thus, to achieve selectivity under kinetic control is very challenging. Herein, we report a novel cobalt-catalyzed regioselective olefin isomerization reaction. By taking the advantage of fine-tunable NNP-pincer ligand structures, this catalytic system features high kinetic control of regioselectivity. This mild catalytic system enables the isomerization of 1,1-disubstituted olefins bearing a wide range of functional groups in excellent yields and regioselectivity. The synthetic utility of this transformation was highlighted by the highly selective preparation of a key intermediate for the total synthesis of minfiensine. Moreover, a new strategy was developed to realize the selective monoisomerization of 1-alkenes to 2-alkenes dictated by installing substituents on the γ-position of the double bonds. Mechanistic studies supported that the in situ generated Co-H species underwent migratory insertion of double bond/β-H elimination sequence to afford the isomerization product. The less hindered olefin products were always preferred in this cobalt-catalyzed olefin isomerization due to an effective ligand control of the regioselectivity for the β-H elimination step.

Iridium-catalyzed carbonyl allylations by allylic alcohols with Tin(II) chloride

Iridium complex [IrCl(cod)]2 can function as a catalyst for the allylation of aldehydes and ketones by allylic alcohols upon addition of an equimolar amount of SnCl2 in THF-H2O; the reaction is carried out between room temperature and 50 °C to give the corresponding homoallylic alcohols. Georg Thieme Verlag Stuttgart.

Development of a highly α-regioselective metal-mediated allylation reaction in aqueous media: New mechanistic proposal for the origin of α-homoallylic alcohols

This paper described a general method to obtain α-adduct homoallylic alcohols using indium, zinc, and tin in water. A new mechanism was proposed to account for the formation of these synthetically difficult-to-obtain molecules. Generally, this method can

Regio- and stereoselective synthesis of homoallylic alcohols based on the use of (3-chloroprop-1-en-1-yl)boronates

A set of (3-chloroprop-1-en-1-yl)boronates 10 were synthesised, starting from (3-chloroprop-1-en-1-yl)bis(isopinocampheyl)borane. Quaternisation of 10 by Grignard methodology afforded "ate" species 14, which underwent spontaneous anionotropic rearrangement to give the substituted allylboronates 15. By a suitable choice of the diol component in 10 and of the reaction temperature, α- or γ-substituted allylboronates 15 or 16 could be selectively produced, offering routes to homoallylic alcohols 9 or anti-8, respectively, after treatment with an aldehyde. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

The first In(OTf)3-catalyzed conversion of kinetically formed homoallylic alcohols into the thermodynamically preferred regioisomers: Application to the synthesis of 22α-sterols

A retro-ene reaction that generates the parent aldehyde and a sigmatropic rearrangement are involved in the In(OTf)3-catalyzed conversion of homoallylic alcohols 1 into the thermodynamically favored regioisomers 2. This method can be used for the stereocontrolled synthesis of linear homoallylic 22α-sterols from their readily accessible branched 22β isomers.

Regioselective reaction of allylbenzotriazoles with aldehydes and ketones in the presence of lithium

The reactions of α- and γ-substituted allylbenzotriazoles 2, 3 and 4 with an excess of lithium in THF at -78°C generate various allyllithiums, which react readily with aldehydes and ketones with high regioselectivity to give predominantly the branched products 5 in excellent yields.

α-Regioselective Carbonyl Allylation by an Allylic Tin Compound Prepared from 1-Bromobut-2-ene and Tin(II) Bromide at a Nonpolar Organic-Aqueous Interface

1-Bromobut-2-ene on a dichloromethane-water biphasic system at 25 deg C causes α-regioselective addition to aldehydes with SnBr2 to produce 1-substituted pent-3-en-1-ols, and causes γ-regioselective addition to aldehydes with SnBr2-Bu4NBr to produce 1-sub