115270-07-0

Upstream product

• 21040-45-9 Cinnamyl acetate 
• 51779-32-9 iminodicarboxylic acid di-tert-butyl ester 
• 17763-67-6 Phenyl triflate 
• 115269-99-3 N,N-bis(tert-butoxycarbonyl)allylamine 
• 4392-24-9 Cinnamyl bromide 
• 108-90-7 chlorobenzene 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 4406-72-8 2-phenyl[1,3,2]dioxaborolane 
• 71-43-2 benzene 
• 85217-69-2 cinnamyl methyl carbonate 
• 106625-69-8 ethyl (E)-3-phenyl-2-propenyl carbonate 

Downstream Products

• 115270-11-6 tert-butyl N-[(2E)-3-phenylprop-2-en-1-yl]carbamate 

Relevant academic research and scientific papers

β-regioselective intermolecular Heck arylation of N,N-disubstituted allylamines

β-Regioselectivity has been demonstrated for the Heck arylation of N,N-disubstituted allylamines. The scope and limitations of the reaction were demonstrated by the coupling of N,N-dibenzylallylamine with a variety of substituted aryl triflates. This methodology represents a straightforward approach for the efficient preparation of a variety of primary β-aryl allyl amines.

Palladium-catalyzed direct arylation of allylamines with simple arenes

The Pd(OAc)2-catalyzed direct C-H bond olefination of unreactive arenes with allylamines in the presence of AgOAc was developed. A variety of allylamines including β-substituted substrates underwent smooth coupling reactions with various arenes

Covalent Organic Framework as a Heterogeneous Ligand for the Regioselective Oxidative Heck Reaction

A simple imine-based covalent organic framework (COF) as heterogeneous ligand for PdII-promoted Heck reaction is reported. Good regioselectivity for a wide range of electronically unbiased olefins is obtained (linear/branched >100:1 in most cases). Related tests and density functional theory calculations are used to explore the reason underlying the high selectivity. This research opens a route for COF as an intriguing platform to control regioselectivity catalysis.

Iridium-catalyzed asymmetric allylic substitutions with bulky amines/oxidative double bond cleavage - Entry into the reetz synthesis of amino alcohols

Branched allylic amines were prepared by Ir-catalyzed enantioselective allylic aminations with the bulky N-nucleophiles HN(Boc)2 and HNBn2. The products were transformed into N-protected amino aldehydes, which were either reduced or coupled diastereoselectively with organometallic compounds to give vicinal amino alcohols. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application. Ir-catalyzed enantioselective allylic aminations with bulky N-nucleophiles HN(Boc)2 and HNBn2 gave N-protected allylic amines, which were transformed into N-protected chiral amino aldehydes. These are useful chiral building blocks as previously demonstrated by Reetz et al. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application.

Palladium-catalyzed highly regioselective Mizoroki-heck arylation of allylamines with aryl chlorides

Palladium catalyst systems for the regioselective Mizoroki-Heck arylation of N,N-diprotected and N-protected allylamines with aryl chlorides have been developed. Pd(OAc)2 in combination with appropriate additives could efficiently catalyze the linear arylation of N,N-diprotected allylamines with aryl chlorides in toluene to give exclusively the γ-arylated products in good to excellent yields and with excellent regio- and stereocontrol and good functional group tolerance. With use of a catalytic mixture of Pd(OAc) 2 and 1,1'-bis(diphenylphosphino)ferrocene, the arylation of N-protected allylamines with aryl chlorides could be accomplished in ethylene glycol/DMSO, which afforded complete β-regioselectivity with good functional group tolerance. The steric and electronic properties of allylamine substrates are found to be critical to the catalytic activity and regiocontrol in both linear and internal arylations. Copyright

Enantioselective syntheses of 2,5-disubstituted pyrrolidines based on iridium-catalyzed allylic aminations-total syntheses of alkaloids from amphibian skins

A broadly applicable route to trans-2,5-disubstituted pyrrolidines has been developed. Key steps are an asymmetric iridium-catalyzed allylic amination, a Suzuki-Miyaura coupling, and an intramolecular aza-Michael addition. Enantiomeric excesses in the range of 93-99 % ee have been achieved. Total syntheses of the alkaloids (-)-225 C, (+)- and (-)-223 H (xenovenine), (+)-223 AB, (+)-195 B, and (+)-223 R have been carried out as applications. Copyright

Salt-free iridium-catalyzed asymmetric allylic animations with N,N-diacylamines and ortho-nosylamide as ammonia equivalents

(Chemical Equation Presented) New variants of the iridium-catalyzed allylic substitution allow N-protected and non-protected chiral allylamines to be prepared with high enantio- and regio-selectivity. The allylamines are used as nucleophiles in highly dia

A new convenient method for the preparation of enamides from N-allylamides

Isomerization of various N-allylamides in the presence of Fe(CO)5 smoothly afforded the corresponding enamides in yields up to 95%. The reported procedure is compatible with various functional groups including protected amino and hydroxy groups. The possible mechanism of transformation is discussed.

Asymmetric Dihydroxylation (AD)/ cyclization of N-diBoc allylic and homoallylic amines: Selective differentiation of the hydroxyl groups

Asymmetric dihydroxylation of N-diBoc protected allylic and homoallylic amines with in situ cyclization affords the corresponding oxazolidinones in good yields. The enantioselectivity is dependent on the substitution pattern of the olefin and ranges from 34-98%. This methodology allows selective differentiation of the hydroxyl groups formed in the AD and increases the potential applications of the resulting products.

The palladium-catalyzed amination of allylic carbonates with di-tert-butyl iminodicarbonate under neutral conditions

N,N-Ditert-butyloxycarbonylallylamines are prepared through a palladium-catalyzed reaction of allylic carbonates with di-tert-butyliminodicarbonate under neutral conditions.Allylic carbonates producing monosubstituted ?-allylpalladium complexes tend to gi