34645-31-3

Upstream product

• 4173-44-8 1-phenyl-1,3-hexadien-5-one 
• 555-31-7 aluminum isopropoxide 
• 58927-78-9 (2E,4E)-1-phenyl-2,4-hexadien-1-ol 
• 79299-29-9 (E)-1-phenyl-1,5-hexadien-3-ol 
• 598-32-3 2-hydroxy-3-butene 
• 4173-44-8 (E,E)-6-phenyl-3,5-hexadien-2-one 

Downstream Products

• 112087-67-9 1,3,3a,4,5,7a-hexahydro-1-methyl-3-oxo-5-phenylisobenzofuran-4-carboxylic acid methyl ester 
• 1071994-45-0 (S,3E,5E)-6-phenylhexa-3,5-dien-2-ol 
• 326804-29-9 (R,3E,5E)-6-phenyl-3,5-hexadien-2-yl acetate 
• 1009809-26-0 ethyl (3E,5E)-6-phenyl-hexadien-2-yl carbonate 
• 1354701-42-0 ((1E,3E)-5-azidohexa-1,3-dienyl)benzene 

Relevant academic research and scientific papers

Polymer-bound palladium-catalyzed coupling of allylic alcohols with hypervalent iodonium salts

The polymer-bound palladium catalyzed cross-coupling reaction of allylic alcohols with hypervalent iodonium sails to form carbon-carbon bonds was achieved at room temperature under extremely mild and aqueous conditions even in the absence of base with very high activity in the Stille coupling reaction. The polymeric catalyst can be easily separated from a reaction mixture and reused more than 10 times with no decrease in activity.

1,n-rearrangement of allylic alcohols promoted by hot water: Application to the synthesis of navenone B, a polyene natural product

It was reported for the first time that hot water as a mildly acidic catalyst efficiently promoted 1,n-rearrangement (n = 3, 5, 7, 9) of allylic alcohols. In some cases, the rearrangement reactions joined isolated C-C double or triple bonds to generate conjugated polyene or enyne structure motifs. We used the 1,3-rearrangement reaction of an allylic alcohol in hot water as part of an attractive new strategy for construction of the polyene natural product navenone B by iterative use of a Grignard reaction, a 1,3-rearrangement of the resulting allylic alcohol, and subsequent oxidation of the rearranged product.

Palladium-catalyzed dienylations of chelated enolates

Isomerization-free reactions of dienyl carbonates with chelated amino acid ester enolates at -78 °C provide important information concerning the mechanism of these dienylations. The formation of regioisomeric products can be explained by competing SN2/SN2′ reactions, and the product distribution can be influenced by the proper choice of the reaction conditions. Chiral allylic substrates show a significant transfer of chirality. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Ruthenium-catalyzed isomerization of homoallylic alcohols in water

Through the catalysis of RuCl2(PPh3)3, the functional groups of homoallylic alcohols are repositioned to give allylic alcohols with controlled regioselectivity. The reaction proceeds most efficiently in an aqueous media. The selectivity in product formation is affected by the reaction temperature and the amount of the catalyst being used. A higher reaction temperature and the use of a smaller amount of the catalyst are preferable for the formation of allylic alcohols. The reaction process was postulated as a tandem olefin migration-allylic rearrangement. Under the same reaction conditions, the functional groups of allylic alcohols undergo allylic rearrangements.