72853-47-5

Upstream product

• 186581-53-3 diazomethane 
• 107-93-7 (E)-but-2-enoic acid 
• 100-52-7 benzaldehyde 
• 3724-65-0 2-butenoic acid 
• 623-43-8 crotonic acid methyl ester 
• 1117-71-1 methyl-4-bromo-2-butenoate 
• 77-78-1 dimethyl sulfate 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 292638-85-8 acrylic acid methyl ester 
• 85636-50-6 1-(trimethylsiloxy)-1-methoxy-1,3-butadiene 
• 3724-55-8 methyl but-3-enoate 

Downstream Products

• 1004960-84-2 5-hydroxy-5-phenyl-pent-2-enoic acid methyl ester 
• 765940-99-6 (R)-(+)-5,6-dihydro-6-phenylpyran-2-one 
• 112607-33-7 (+)-(R)-δ-(phenyl)-δ-valerolactone 
• 4660-17-7 rac-6-phenyl-5,6-dihydro-2H-pyran-2-one 
• 10413-17-9 6-phenyltetrahydropyran-2-one 
• 37464-83-8 methyl 5-hydroxy-5-phenylpentanoate 
• 112022-82-9 (5R) methyl 5-hydroxy-5-phenylpentanoate 

Relevant academic research and scientific papers

One-pot vinylogous aldol addition of β,γ-unsaturated esters under mild conditions

We described a one-pot vinylogous aldol addition of methyl 3-butenoate to aromatic aldehydes in the presence of silver salts and the TMSCl-TBAF mixture. The reaction can be done simply by sequentially mixing reagents in situ, and it does not require any c

Enzyme mediated kinetic resolution of δ-hydroxy-α,β-unsaturated esters as a route to optically active δ-lactones

A novel synthetic route to optically active saturated and unsaturated δ-lactones based on enzymatic kinetic resolution and ring-closing metathesis reactions has been proposed. The influence of temperature, co-solvent, organic additives and the substrate s

Diastereoselective synthesis of trifluoromethylated 1,3-dioxanes by intramolecular oxa-Michael reaction

A highly diastereoselective synthesis of trifluoromethylated 1,3-dioxanes is described. The reaction proceeds by an addition/oxa-Michael sequence and works efficiently under mild reaction conditions, with a good substrate scope and acceptable to good yiel

The vinylogous aldol reaction of unsaturated esters and enolizable aldehydes using the novel Lewis acid aluminum tris(2,6-di-2-naphthylphenoxide)

The synthesis of the novel Lewis acid, aluminum tris(2,6-di-2- naphthylphenoxide) (ATNP), and its use in the vinylogous aldol reaction between methyl crotonate and enolizable aldehydes are described. ATNP is related to Yamamoto's Lewis acid, aluminum tris(2,6-diphenylphenoxide) (ATPH), but the 2-naphthyl groups more effectively block the α-position of aldehydes, enabling the selective enolization of crotonate esters in the presence of enolizable aldehydes. Vinylogous aldol reactions then proceed smoothly and in high yields with a variety of substrates.

Molecular recognition of α,β-unsaturated carbonyl compounds using aluminum tris(2,6-diphenylphenoxide) (ATPH): Structural and conformational analysis of ATPH complexes and application to the selective vinylogous aldol reaction

Various α,β-unsaturated carbonyl compounds were coordinated with aluminum tris(2,6-diphenylphenoxide) (ATPH) to give the corresponding Lewis acid-base complexes in a distinctive coordination fashion (selective coordination). ATPH recognizes carbonyl substrates and subsequently orients itself as it forms a stable complex through selective coordination with the carbonyl oxygen. Selective coordination also confers a conformational preference to each carbonyl compound under the steric and electronic influence of ATPH, which enables the vinylogous aldol reaction of α,β-unsaturated carbonyl compounds to give the corresponding γ-aldol products with different regio- and stereoselectivities.

Enantioselective syntheses of cryptocarya triacetate, Cryptocaryolone, and cryptocaryolone diacetate

(Matrix presented) The enantioselective syntheses of three natural products from Cryptocarya latifolia have been achieved in 13-15 steps from ethyl sorbate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-cat

Mixed crossed aldol condensation between conjugated esters and aldehydes using aluminum tris(2,6-diphenylphenoxide)

The combined use of aluminum tris(2,6-diphenylphenoxide) (ATPH) and lithium 2,2,6,6-tetramethylpiperidide (LTMP) has proven to be effective for the mixed crossed aldol condensation between conjugated esters and various aldehydes. An example is shown in Eq

Cadmium chloride mediated regiocontrol of dienolates and ketene thioacetals: γ condensation with aldehydes

The use of cadmium chloride to control the regioselectivity of vinylogous anions upon condensation with aldehydes is described.Addition occurred preferentially at the γ position with substituted crotonates and 2-ethylidene-1,3-dithiane (6).Experiments dem

REFORMATSKY REACTION USING Zn/Ag COUPLE

The Reformatsky reaction is easy to run in ethereal solvents in the presence of Zn/Ag couple.From methyl γ-bromocrotonate and krtones, remified esters are fromed in refluxing Et2O, linear ones in refluxing THF.

Dienediolates from Unsaturated Carboxylic Acids. Reaction with para-Substituted Benzaldehydes. Electronic Effects on Regioselectivity

Regioselectivity α/γ ratios for addition of the lithium dienediolate of crotonic acid to para-substituted benzaldehydes are subject to small electronic effects when reactions are carried out at low temperature, but strong influence by substituents is observed on heating for 1 h at 60 deg C.A linear correlation is then found between regiochemical ratios and ?p parameters.Stereoselectivity RR/RS ratios (33:66 to 43:57) for α-adducts obtained in the cold do not depend on the substituents.