34097-95-5

Upstream product

• 82263-47-6 (2S,3R,4S,5R)-3,4-Dimethyl-5-phenyl-2-((E)-styryl)-oxazolidine 
• 14371-10-9 (E)-3-phenylpropenal 
• 557-20-0 diethylzinc 
• 925-90-6 ethylmagnesium bromide 
• 78-79-5 isoprene 
• 384333-59-9 (E)-3-phenyl-pent-2-en-1-ol 
• 764-38-5 (3Z)-pent-3-en-1-ol 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 110-62-3 pentanal 
• 940-52-3 3-phenyl-2-propenyl vinyl ether 
• 104-54-1 3-Phenylpropenol 
• 425-75-2 trifluoromethanesulfonic acid ethyl ester 
• 104-55-2 3-phenyl-propenal 

Downstream Products

• 2845-28-5 (+/-)-3-phenylpentan-1-ol 

Relevant academic research and scientific papers

Catalytic C-H Arylation of Aliphatic Aldehydes Enabled by a Transient Ligand

The direct arylation of aliphatic aldehydes has been established via Pd-catalyzed sp3 C-H bond functionalization in the presence of 3-aminopropanoic acids as transient directing groups. The reaction showed excellent functional group compatibility and chemoselectivity in which a predominant preference for functionalizing unactivated β-C-H bonds of methyl groups over others was achieved. In addition, C-H bonds of unactivated secondary sp3 carbons can also be functionalized. The extreme popularity and importance of aliphatic aldehydes would result in broad applications of this novel method in organic chemistry and medicinal sciences.

Enantioselective redox-relay oxidative heck arylations of acyclic alkenyl alcohols using boronic acids

A general, highly selective asymmetric redox-relay oxidative Heck reaction using achiral or racemic acyclic alkenols and boronic acid derivatives is reported. This reaction delivers remotely functionalized arylated carbonyl products from acyclic alkenol substrates, with excellent enantioselectivity under mild conditions, bearing a range of useful functionality. A preliminary mechanistic investigation suggests that the regioselectivity of the initial migratory insertion is highly dependent on the electronic nature of the boronic acid and more subtle electronic effects of the alkenyl alcohol.

Iridium-catalyzed isomerization of primary allylic alcohols under mild reaction conditions

The isomerization of primary allylic alcohols into the corresponding aldehydes has been accomplished using an analogue of Crabtree's iridium hydrogenation catalyst and by adequately tuning the experimental conditions. A wide range of substrates is converted quantitatively into the desired aldehyde at room temperature in expedient reaction times by using catalyst loading as low as 0.25 mol %.

Iridium-catalyzed isomerization of primary allylic alcohols

A readily accessible iridium hydrogenation catalyst displays high reactivity for the isomerization of primary allylic alcohols under mild reaction conditions. Key to the efficiency of the catalytic system is to deviate from the conventional hydrogenation route in favor of the desired isomerization pathway by adequately tuning the reaction conditions as indicated by preliminary mechanistic investigations. Schweizerische Chemische Gesellschaft.

Palladium- and copper-catalyzed 1,4-additions of organozinc compounds to conjugated aldehydes

Conjugated aldehydes undergo smooth Pd(OAc)2·PPh 3- or Me2CuCNLi2-catalyzed 1,4-addition of dialkylzinc reagents.

Regio- and stereoselective nickel-catalyzed homoallylation of aldehydes with 1,3-dienes

Ni(acac)2 catalyzes homoallylation of aldehydes with 1,3-dienes in the presence of triethylborane. Triethylborane serves as a reducing agent delivering a formal hydride to the C2 position of 1,3-dienes, thus generating a formal homoallyl anion species and enabling the novel homoallylation of aldehydes. The reaction proceeds smoothly at room temperature in the absence of any phosphane or nitrogen ligands and is highly regioselective and stereoselective for a wide variety combination of aldehydes and 1,3-dienes: e.g., isoprene and benzaldehyde combine to give a mixture of anti- and syn-1-phenyl-3-methyl-4-penten-1-ol (2.2) in a ratio of 15:1 in 90% yield. Under the conditions, sterically congested aliphatic aldehydes and ketones show low yields. In such cases, diethylzinc serves as a substitute for triethylborane and yields the expected products in good yields with similarly high regio- and stereoselectivity. 1,3-Cyclohexadiene is one exception among 24 kinds of dienes examined and undergoes allylation (not homoallylation) selectively.

Effect of InCl3 on the addition of Grignard reagents to α,β-unsaturated carbonyl compounds

Control of 1,2- versus 1,4-addition of organometallic reagents to enones remains a long-standing problem. There is still no satisfactory 1,2-directing agent comparable to the 1,4-directing effect of copper salts. We report that the presence of just 5 mol% indium(III) chloride can significantly alter the amount of 1,2-product formed in these reactions.

Nickel-catalyzed homoallylation of adelhydes and ketones with 1,3- dienes and complementary promotion by diethylzinc or triethylborane

Regio- and stereoselective homoallylation of saturated aldehydes and ketones to give biohomoallyl alcohols 1,3-anti-1 is achieved with [Ni(acac)2] (cat.) and Et2Zn [Eq. (a)]. This new catalyst system thus complements the previously reported combination of [Ni(acac)2] with Et3B, which offers advantages in the homoallylation of unsaturated and aromatic aldehydes. acac = acetylacetonato.

Arene-catalysed lithiation of triflates and triflamides under Barbier-type conditions: An indirect transformation of alcohols and amines into organolithium compounds

The reaction of alkyl triflates 1 or benzyl triflamides 3 with an excess of lithium powder and a catalytic amount of naphthalene (4 mol%) in the presence of different electrophiles [Me3SiCl, Pr(i)CHO, Bu(t)CHO, PhCHO, 4-MeOC6H4-CHO, CH3(CH2)6CHO, Et2CO, (CH2)5CO, (c-C3H5)2CO, PhCOMe, 4-MeC6H4COPh, PhCh=NPh, n-C8H7CON(CH2)4] in THF at temperature ranging between -78 and 0°C leads, after hydrolysis with water, to the corresponding condensation products 2. When α,β-unsaturated carbonyl compounds are used as electrophilic compounds 1,2- (3-cyclohexenone) or 1,4-addition (cinnamaldehyde or benzylideneacetone) takes place depending on the electrophile used.

ADDITION D'ORGANOCUPRATES AUX OXAZOLIDINES CHIRALES α-β ETHYLENIQUES : I - RESULTATS - EFFETS DE SEL ET DE SOLVANT

Organocuprates add quantitatively to oxazolidines I.The steric course of the reaction can be reversed and the diastereoselectivity enhanced by salt effect and (or) by solvent effect.