73249-15-7

Upstream product

• 134962-95-1 4-methyl-6-phenyl-5,6-dihydro-2H-pyran-2-ol 
• 100-52-7 benzaldehyde 
• 57132-28-2 (E)-2-methyl-4-phenylbut-3-en-2-ol 
• 68-12-2 N,N-dimethyl-formamide 
• 123-73-9 trans-Crotonaldehyde 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 42599-24-6 E-styryl iodide 
• 54340-95-3 1,1-diethoxy-3-methyl-3-butene 
• 114968-77-3 lithio-1 methyl-2 trimethylsiloxy-4 butadiene 
• 78108-48-2 2-lithio-1-trimethylsiloxyethylene 
• 1896-62-4 (E)-benzalacetone 
• 145572-39-0 1-bromo-4,4-diethoxy-2-methylbut-1-ene 
• 145572-38-9 1,2-dibromo-4,4-diethoxy-2-methylbutane 
• 151018-50-7 1-bromo-4-ethoxy-2-methylbuta-1,3-diene 

Downstream Products

• 1377848-03-7 (R,E)-6-phenyl-4-styryl-6-(trifluoromethyl)-5,6-dihydro-2H-pyran-2-one 
• 942416-34-4 (S)-(-)-3-methyl-5-phenylpentanaldehyde 
• 41927-33-7 (S)-(-)-3-methyl-5-phenylpentan-1-ol 
• 1537904-32-7 (3R,5S)-3,5-diphenyl-7-((E)-styryl)-2,3,5,6-tetrahydropyrazolo[1,2-a][1,2]diazepine-1,9-dione 
• 1003580-04-8 3-methyl-5-phenyl-2,4-pentadienoic acid 

Relevant academic research and scientific papers

Oxidative γ-addition of enals to trifluoromethyl ketones: Enantioselectivity control via lewis acid/n-heterocyclic carbene cooperative catalysis

An oxidative γ-functionalization of enals under N-heterocyclic carbene (NHC) catalysis to give unsaturated δ-lactones is disclosed. Enantioselectivity control involving the relatively remote enal γ-carbon was achieved via Lewis acid [Sc(OTf)3 or combined Sc(OTf) 3/Mg(OTf)2] and NHC cooperative catalysis.

Heck reactions of crotonaldehyde

A direct method for the synthesis of β,β-disubstituted-α, β-unsaturated aldehydes via Heck reaction of aryl halides with crotonaldehyde and related substrates has been developed. The reaction provides rapid access to products usually prepared via multistep sequences. The power of the method in combination with an organocatalytic transfer hydrogenation is illustrated with a short asymmetric synthesis of (S)-Florhydral. Georg Thieme Verlag Stuttgart.

HISTONE DEACETYLASE INHIBITORS

Hormone refractory metastatic disease can be treated with an oxyamide-containing compound through the inhibition of HDAC1 or HDAC2.

Obtention of 2,2-(diethoxy) vinyl lithium and 2-methyl-4-ethoxy butadienyl lithium by Arene-catalysed lithiation of the corresponding chloro derivatives. Synthetic applications

Vinylic lithium reagents 1 and 2 could be obtained by the title procedure from their chloro precursors 5 and 6 instead of the less stable corresponding bromo derivatives 3 and 4. Condensation with carbonyl compounds leads to interesting synthetic applications such as a two steps synthesis of retinal 13 from β-cyclocitral 10.

Polyvinylogation Reagents: 1-Lithio-4-trimethylsiloxy-penta-1,3-diene and 1-Lithio-4-ethoxy-2-methyl-buta-1,3-diene

Title products, lithiodienol ethers 6a and 7a, synthetic equivalents of 4-lithio pent-3-ene-2-one and 4-lithio-senecialdehyde were obtained by bromine-lithium exchange.They are choice reagents for the transformations 1 -> 2 and 1 -> 3, respectively.

A New Prenylation Method using the Lithium Enolate of Prenal. Reaction with Aldehydes and α,β-Unsaturated Aldehydes

A γ-condensation of the enolate of prenal 1 is observed with aldehydes and α,β-unsaturated aldehydes.In this case, a conjugate addition is obtained.Intermediate dihydropyrans 4 yield dienals 5 by hydrolysis.Keywords: Lithium enolate of prenal, dihydropyrans, dienals, γ-addition, prenylation.

UN NOUVEAU REACTIF DE PRENYLATION : LE LITHIO-1 METHYL-2 TRIMETHYLSILOXY-4 BUTADIENE

This new reagent is obtained by bromine-lithium exchange using tertiobutyllithium in ether at -70 deg C.Its condensation with carbonyl compounds followed by hydrolysis in mild conditions leads to polyenals with good yields.Synthesis of retinal from β-ionylidenacetaldehyde is described.