53384-66-0

Upstream product

• 2396-84-1 ethyl hexa-2,4-dienoate 
• 57006-69-6 (E,E)-sorbyl acetate 
• 51795-88-1 1-bromo-10-(tetrahydropyranyloxy)decane 

Downstream Products

• 53398-76-8 (2E,4Z)-hexa-2,4-dien-1-al 
• 871506-32-0 (2E,4Z)-2,4-hexadienoic acid pentafluorophenyl ester 
• 871506-36-4 (3R,5R)-3-tert-Butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-6-((2E,4Z)-hexa-2,4-dienoylamino)-hexanoic acid pentafluorophenyl ester 
• 30361-30-9 (2E,4Z)-2,4-hexadienoic acid 
• 118575-55-6 (2E,4Z)-2,4-hexadienyl 2-diazo-4-phenyl-3-butenoate 
• 118575-63-6 (3aα,6β,7α)-(+/-)-3,3a,6,7-tetrahydro-6-methyl-7-phenyl-1H-cycloheptafuran-1-one 
• 142-83-6 trans,trans-2,4-Hexadienal 
• 54716-12-0 (2Z,4E)-hexa-2,4-dienal 
• 118575-47-6 (2E,4Z)-2,4-hexadienyl 4-phenyl-3-butenoate 

Relevant academic research and scientific papers

Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols

By using copper(I) homoenolates as nucleophiles, which are generated through the ring-opening of 1-substituted cyclopropane-1-ols, a catalytic asymmetric allylic substitution with allyl phosphates is achieved in high to excellent yields with high enantioselectivity. Both 1-substituted cyclopropane-1-ols and allylic phosphates enjoy broad substrate scopes. Remarkably, various functional groups, such as ether, ester, tosylate, imide, alcohol, nitro, and carbamate are well tolerated. Moreover, the present method is nicely extended to the asymmetric construction of quaternary carbon centers. Some control experiments argue against a radical-based reaction mechanism and a catalytic cycle based on a two-electron process is proposed. Finally, the synthetic utilities of the product are showcased by means of the transformations of the terminal olefin group and the ketone group.

An Approach to Cytochalasan Synthesis: Macrolide Formation by an Intramolecular Diels-Alder Reaction. X-Ray Structure of Methyl (1RS, 2SR, 5RS, 6RS)-2,5-Dimethyl-1-hydroxy-6-cyclohex-3-ene-1-carboxylate

When heated in toluene under reflux, under high dilution conditions, trans,trans-hexadeca-12,14-dienoyl-oxymaleic anhydride (4) cyclised via an intramolecular Diels-Alder reaction to give the macrocyclic lactone (5) in 27percent yield together with 5percent of a regioisomer (23). (1RS, 2SR, 5RS, 6RS)-2,5-Dimethyl-1-octanoyloxycyclohex-3-ene-1,6-dicarboxylic acid anhydride (11) was converted into the methyl (1RS, 2SR, 5RS, 6RS)-2,5-dimethyl-1-octanoyloxy-6-benzylcarbonylcyclohex-3-ene-1-carboxylate (33), but selective reduction of this ketone was unsuccessful.The structure of one of the reduction products, methyl (1RS, 2SR, 5RS, 6RS)-2,5-dimethyl-1-hydroxy-6-cyclohex-3-ene-1-carboxylate (35) was confirmed by an X-ray structure determination.