87802-78-6

Upstream product

• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 108-59-8 malonic acid dimethyl ester 
• 18424-76-5 dimethyl malonate sodium salt 
• 160879-62-9 methyl 1-phenylprop-2-enyl carbonate 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 21040-45-9 Cinnamyl acetate 
• 106625-69-8 ethyl (E)-3-phenyl-2-propenyl carbonate 
• 106625-70-1 ethyl (1-phenylallyl) carbonate 
• 86537-61-3 ethyl cinnamylcarbonate 
• 85217-69-2 cinnamyl methyl carbonate 
• 2687-12-9 cinnamyl chloride 
• 100-52-7 benzaldehyde 
• 104-54-1 3-Phenylpropenol 
• 124-41-4 sodium methylate 

Downstream Products

• 1255767-99-7 C₁₇H₁₈O₄ 
• 675855-26-2 (R)-(+)-3-phenyl-4-pentenoic acid 
• 1217596-54-7 (R)-2-phenylbut-3-en-1-amine 
• 1217596-66-1 (2R)-N-(3-(6,10-dioxaspiro[4.5]decan-1-yl)propyl)-2-phenylbut-3-en-1-amine 
• 1217596-64-9 (2R)-N-(2-(1,5-dioxaspiro[5.5]undecan-7-yl)ethyl)-2-phenylbut-3-en-1-amine 

Relevant academic research and scientific papers

Cobalt-Catalyzed Allylic Alkylation Enabled by Organophotoredox Catalysis

Co-catalyzed allylic substitution reactions have received little attention, arguably because of the lack of any known advantage of Co catalysis over either Rh or Ir catalysis. Described here is a general and regioselective Co-catalyzed allylic alkylation using an in situ catalyst activation by organophotoredox catalysis. This noble-metal-free catalytic system exhibits unprecedentedly high reactivities and regioselectivities for the allylation with an allyl sulfone, for the first time, representing the unique synthetic utility of the Co-catalyzed method compared to the related Rh- and Ir-catalyzed reactions.

Enantioselective Ir-Catalyzed Allylic Alkylation of Racemic Allylic Alcohols with Malonates

Ir-catalyzed enantioselective allylic alkylation of branched racemic allylic alcohols with malonates is described. Enabled by Carreira's chiral Ir/(P, olefin) complex, the method described allows allylic substitution with various aromatic alcohols and mal

An improved class of phosphite-oxazoline ligands for Pd-catalyzed allylic substitution reactions

A method for generation of Pd/phosphite-oxazoline catalysts containing an alkyl backbone chain has been successfully applied to Pd-catalyzed allylic substitution reactions. By carefully selecting the substituents at both the alkyl backbone chain and the oxazoline of the ligand, as well as the configuration of the biaryl phosphite group, high activities (TOF > 8000 mol substrate × (mol Pd × h)?1) and excellent enantioselectivities (ee's up to 99%) have been achieved for many hindered and unhindered substrates with a wide range of C-, O-, and N-nucleophiles (73 substitution products in total). Moreover, DFT and NMR studies of the key Pd-allyl complexes allowed us to better understand the origin of the excellent enantioselectivities observed experimentally. The useful application of the Pd/phosphite-oxazoline catalysts was demonstrated by the syntheses of many chiral carbobicycles, with multiples stereocenters, by simple sequential reactions involving Pd-allylic substitution and either 1,6-enyne cyclization or Pauson?Khand enyne cyclization.

Regio- and Enantioselective Rhodium-Catalyzed Allylic Alkylation of Racemic Allylic Alcohols with 1,3-Diketones

Highly regio- and enantioselective rhodium-catalyzed allylic alkylation of 1,3-diketones with racemic secondary allylic alcohols is reported. In the presence of a Rh-catalyst derived from the Carreira (P, olefin)-ligand and TFA as an additive, chiral branched α-allylated 1,3-diketones could be obtained in good to excellent yields, with excellent regio- and enantioselectivity (b/l > 19/1, 86-98% ee). The direct utilization of allyl alcohols as electrophiles represents an improvement from the viewpoint of an atom economy. Both aryl- and aliphatic-substituted allyl alcohols are suitable substrates with excellent reaction outcomes. This reaction features mild conditions, broad substrate scope, and readily available substrates.

Iridium/ N-Heterocyclic Carbene Complex-Catalyzed Intermolecular Allylic Alkylation Reaction

N-Heterocyclic carbenes (NHCs) were found to be suitable ligands in Ir-catalyzed intermolecular allylic alkylation reaction. In the presence of a catalyst derived from [Ir(dncot)Cl]2 (dncot = dinaphthocyclooctatetraene) and triazolium salt L7,

Efficient stereochemical communication in phosphine-amine palladium-complexes: Exploration of N-substituent effects in coordination chemistry and catalysis

Six-membered chelate complexes of type [Pd(1a-e)Cl2] (2a-e) and [Pd(1a-e)(η3-PhCHCHCHPh)]BF4 (3a-e) of a series of systematically varied chiral phosphine-amine ligands (S,S)-Ph2PCH(CH3)CH2C

Palladium-Based Supramolecularly Regulated Catalysts for Asymmetric Allylic Substitutions

Herein is reported the effect of different polyether binders (alkali metal, alkaline earth metal, and lanthanide salts) as regulation agents to enhance the catalytic properties of palladium complexes derived from enantiopure bisphosphite ligands in allyli

Conformational Preferences of a Tropos Biphenyl Phosphinooxazoline-a Ligand with Wide Substrate Scope

Excellent enantioselectivities are observed in palladium-catalyzed allylic substitutions of a wide range of substrate types and nucleophiles using a bidentate ligand composed of oxazoline and chirally flexible biaryl phosphite elements. This unusually wid

Diphosphorus Ligands Containing a P-Stereogenic Phosphane and a Chiral Phosphite or Phosphorodiamidite – Evaluation in Pd-Catalysed Asymmetric Allylic Substitution Reactions

The synthesis of 14 new optically pure C1-symmetric phosphane–phosphinite (1–4), phosphane–phosphite (5–9) and phosphane–phosphorodiamidite (10–14) ligands is reported. The ligands were prepared through the condensation of (2-hydroxyphenyl)phenylphosphanes PPh(2-PhOH)R (R = Me, tBu and Ph) with chlorodiisopropylphosphane (1 and 2), chlorodiphenylphosphane (3 and 4), the chlorodioxaphosphepine derived from both enantiomers of 1,1′-bi-2-naphthol (5–9) and the chlorodiazaphosphepine derived from both enantiomers of N,N′-dimethyl-1,1′-binaphthyl-2,2′-diamine (10–14) in the presence of a base. With these ligands, cationic Pd complexes of the type [Pd(η3-C4H7)(PP′)]PF6(Pd1–Pd14) were obtained and characterised; the crystal structures of Pd1, Pd2 and Pd13 were obtained. In solution, the complexes are present as mixtures of two diastereomers because of the lack of symmetry of the ligand and the presence of the methallyl group. The Pd complexes catalyse the allylic alkylation with dimethyl malonate and the amination with benzylamine of the model substrate rac-3-acetoxy-1,3-diphenyl-1-propene (I). For the alkylation, full conversions and good enantioselectivities (up to 96 % ee with Pd14) were observed.

Palladium-catalyzed enantioselective allylic substitution in the presence of monodentate furanoside phosphoramidites

A library of monodentate furanoside phosphoramidites, easily synthesized from inexpensive D-xylose and optically pure 1,1-bi-2-naphthol (BINOL), was used as ligands for the palladium-catalyzed allylic alkylation and amination. The matched pair was formed from D-xylose-derivatives and (S)-BINOL. The asymmetric induction depends strongly on the substituent at the C5 of the carbohydrate backbone; both bulky 5-O-pivaloyl and 5-deoxy derivatives gave excellent results, whereas ligands with trityl protection at position C5 induced low ee values with reversal of configuration. The solvent used for the addition is also of great importance with highest enantioselectivities observed in diethyl ether. The best results for both alkylation and amination, up to 98-99 ee, were obtained for sterically demanding allylic acetates. Single is better: New carbohydrate ligands bearing a single 1,1-bi-2-naphthol (BINOL)-derived phosphoramidite moiety are developed and successfully applied to the palladium-catalyzed asymmetric allylic substitution. The enantioselectivities are equal or better than those obtained for similar systems containing two BINOL moieties and reach up to 99 ee.