79801-99-3

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 108-94-1 cyclohexanone 
• 4392-24-9 Cinnamyl bromide 
• 137595-05-2 bromure de cinnamylzinc 
• 54962-99-1 cinnamyllithium 
• 2687-12-9 cinnamyl chloride 
• 101306-31-4 benzyl cinnamyl ether 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 21040-45-9 Cinnamyl acetate 
• 103-54-8 cinnamyl acetate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 221006-77-5 cinnamylboronic acid 
• 104-54-1 3-Phenylpropenol 
• 85217-69-2 cinnamyl methyl carbonate 

Downstream Products

• 5449-68-3 2-(1-hydroxycyclohexyl)-2-phenylacetic acid 

Relevant academic research and scientific papers

Nickel-catalyzed reductive allylation of ketones with allylic carbonates

Nickel-catalyzed efficient umpolung allylation of ketones with allylic carbonates in the presence of zinc powder is developed, which accommodates a variety of allylic and ketone substrates. Although chiral ligand is necessary for the transformation, no enantioselectivity was observed. Georg Thieme Verlag Stuttgart New York.

Highly regioselective iridium-catalyzed and samarium-promoted coupling of allylic carbonates with ketones: A new approach towards homoallylic alcohols

A highly regioselective Ir-catalyzed and Sm-promoted coupling of allylic carbonates with ketones has been realized, which provides the homoallylic alcohols in up to 89% yields. This strategy gives a convenient method for the synthesis of liquid crystals with a mono-fluorinated quaternary carbon chain. The Royal Society of Chemistry 2013.

Palladium-catalyzed synthesis and isolation of functionalized allylboronic acids: Selective, direct allylboration of ketones

Allyl boronates are very important reagents in advanced organic synthesis for the allylation of carbonyl compounds[1] and in cross-coupling[2] reactions. A practically unrivalled property of allylboronates is their highly regio- and stereoselective additi

Arene-catalysed lithiation of phenyl- and 1,1-diphenylcyclopropane: synthetic applications

The reaction of phenylcyclopropane (1) with an excess of lithium and a catalytic amount of DTBB (2.5% molar) in THF at room temperature, followed by treatment with an electrophile [Me3SiCl, PhMe2SiCl, t-BuCHO, PhCHO, Me2CO

Petasis borono-Mannich reaction and allylation of carbonyl compounds via transient allyl boronates generated by palladium-catalyzed substitution of allyl alcohols. An efficient one-pot route to stereodefined α-amino acids and homoallyl alcohols

An efficient one-pot procedure was designed by integration of the pincer-complex-catalyzed borylation of allyl alcohols in the Petasis borono-Mannich reaction and in allylation of aldehydes and ketones. These procedures are suitable for one-pot synthesis of α-amino acids and homoallyl alcohols from easily available allyl alcohol, amine, aldehyde, or ketone substrates. In the presented transformations, the active allylating agents are in situ generated allyl boronic acid derivatives. These transient intermediates are proved to be reasonably acid-, base-, alcohol-, water-, and air-stable species, which allows a high level of compatibility with the reaction conditions of the allylation of various aldehyde/ketone and imine electrophiles. The boronate source of the reaction is diboronic acid or in situ hydrolyzed diboronate ester ensuring that the waste product of the reaction is nontoxic boric acid. The regio- and stereoselectivity of the reaction is excellent, as almost all products form as single regio- and stereoisomers. The described procedure is suitable to create quaternary carbon centers in branched allylic products without formation of the corresponding linear allylic isomers. Furthermore, products comprising three stereocenters were formed as single products without formation of other diastereomers. Because of the highly disciplined consecutive processes, up to four-step, four-component transformations could be performed selectively as a one-pot sequence. For example, stereodefined pyroglutamic acid could be prepared from a simple allyl alcohol, a commercially available amine, and glyoxylic acid in a one-step procedure. The presented method also grants an easy access to stereodefined 1,7-dienes that are useful substrates for Grubbs ring-closing metathesis.

Iron-catalyzed allylation of ketones

Allylation of ketones has been efficiently performed using iron-complex catalysis and led to homoallylic alcohols in high yields.

Reductive coupling of allylic esters with carbonyl compounds mediated by the mischmetall/[SmI2/Pd0cat.′] cat. system

The mischmetall/[SmI2/Pd0cat.′] cat. system has been used to mediate the allylation of ketones using a variety of allylic esters (acetates, carbonates and phosphates). Thus, a "two-stage catalysis" has been carried out using SmI2 and Pd(PPh3)4 in catalytic amounts together with mischmetall (an alloy of the light lanthanides) as a co-reductant. A catalytic scheme that takes into account previously reported reactions of SmI2/Pd 0cat. and mischmetall/SmI2,Cat. systems is proposed. It has also been shown that palladium complexes catalyse the addition of organolanthanide species to ketones. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Pd-catalyzed nucleophilic allylic alkylation of aliphatic aldehydes by the use of allyl alcohols

Under catalysis of Pd(OAc)2-(P-n-Bu)3, Et 2Zn promotes a variety of allyl alcohols to undergo nucleophilic allylation of aliphatic aldehydes and ketones at room temperature and provides homoallyl alcohols in 60-90 and ca. 60% isolated yield, respectively. The reaction is irreversible and kinetically controlled, and unique regio- and stereoselectivities observed for the allylation with unsymmetrically substituted allyl alcohols are discussed.

Allylation of carbonyl compounds by allylic acetates using a cobalt halide as catalyst

In acetonitrile as solvent and in the presence of a simple cobalt halide as catalyst, the reduction by zinc dust of a mixture of aldehydes or ketones and allylic acetates affords the corresponding homoallylic alcohols in good yields.

Iron-catalyzed electrochemical allylation of carbonyl compounds by allylic acetates

Homoallylic alcohols were synthesized from aldehydes or ketones and allylic acetates, using an electrochemical process catalyzed by iron complexes. We first studied the reactivity of allyl acetate, using N,N-dimethylformamide (DMF) or acetonitrile (AN) as solvent, FeBr2 as catalyst, and Fe as the sacrificial anode. Then we tested the regioreactivity of crotyl acetate and other allylic derivatives.