111464-55-2

Upstream product

• 591-87-7 Allyl acetate 
• 130203-11-1 (S)-2-[(Diphenylphosphanyl)-methyl]-1-((Z)-2-phenyl-propenyl)-pyrrolidine 
• 583-04-0 vinyl benzoate 
• 15727-80-7 allyl 4-nitrobenzoate 
• 4873-09-0 allyl tosylate 
• 130203-10-0 allyl o-toluenesulfonate 
• 128402-81-3 (S)-3-Methyl-2-[2-phenyl-prop-(E)-ylideneamino]-butyric acid allyl ester 
• 124006-29-7 (S)-1-((Z)-2-Phenyl-propenyl)-pyrrolidine-2-carboxylic acid allyl ester 
• 106-95-6 allyl bromide 
• 107-05-1 3-chloroprop-1-ene 
• 128402-81-3 (S)-3-Methyl-2-[2-phenyl-prop-(E)-ylideneamino]-butyric acid allyl ester 
• 128402-82-4 (2S,3S)-3-Methyl-2-[2-phenyl-prop-(E)-ylideneamino]-pentanoic acid allyl ester 
• 128402-79-9 (S)-3-Phenyl-2-[2-phenyl-prop-(E)-ylideneamino]-propionic acid allyl ester 
• 34713-70-7 2-Phenylpropanal 

Downstream Products

• 116002-30-3 (S)-2-methyl-2-phenylpent-4-en-1-ol 
• 1301717-40-7 (S)-2-methyl-1,2-diphenylpent-4-en-1-one 
• 440369-03-9 (3S)-3-methyl-4-oxo-3,4-diphenylbutanal 
• 1301717-38-3 C₁₈H₂₀O 

Relevant academic research and scientific papers

Palladium-catalyzed asymmetric allylations of chiral enamines bearing phosphine functionality. Effects of anionic counterparts of allylating reagents on asymmetric induction

Palladium-catalyzed asymmetric allylations of chiral enamines bearing a phosphine group were attempted using various allylating reagents to produce optically active α-allyl carbonyl compounds. The great effects of the anionic counterparts of the allylatin

Organocatalytic Asymmetric α-Allylation and Propargylation of α-Branched Aldehydes with Alkyl Halides

Enantioselective α-allylation and -propargylation of α-branched aldehydes with alkyl halides was successfully performed using a chiral primary amino acid organocatalyst. This alkylation reaction, involving the generation of a chiral quaternary carbon stereocenter, proceeded smoothly in a mildly basic aqueous solution of potassium hydrogen carbonate to furnish α-allylated or -propargylated aldehydes in a good yield (up to 87%) and high enantioselectivity (up to 96% ee).

Asymmetric α-allylation of α-branched aldehydes with allyl alcohols by synergistic catalysis using an achiral palladium complex and a chiral primary amino acid

Highly enantioselective direct α-allylation of α-branched aldehydes with simple allyl alcohols was achieved by the combined use of an achiral transition-metal catalysis with a palladium complex and a chiral organocatalysis with a readily obtainable primary α-amino acid. Various α-allylated aldehydes possessing a stereocontrolled quaternary carbon stereogenic center were synthesized in high yields with high enantioselectivity. Georg Thieme Verlag Stuttgart New York.

Counterion-Enhanced Pd/Enamine Catalysis: Direct Asymmetric α-Allylation of Aldehydes with Allylic Alcohols by Chiral Amines and Achiral or Racemic Phosphoric Acids

We report a straightforward and efficient Pd/enamine catalytic procedure for the direct asymmetric α-allylation of branched aldehydes. The use of simple chiral amines and easily prepared achiral or racemic phosphoric acids, together with a suitable Pd-source resulted in a highly active and enantioselective catalyst system for the allylation of various α-branched aldehydes with different allylic alcohols. The reported procedure could provide an easy access to both product antipodes. Furthermore, two possible orthogonal derivatizations of the enantioenriched aldehydes were performed without any decrease in enantioselectivity.

Asymmetric α-Allylation of Aldehydes with Alkynes by Integrating Chiral Hydridopalladium and Enamine Catalysis

A palladium-catalyzed asymmetric α-allylation of aldehydes with alkynes has been established by integrating the catalysis of enamine and chiral hydridopalladium complex that is reversibly formed from the oxidative addition of Pd(0) to chiral phosphoric acid. The ternary catalyst system, consisting of an achiral palladium complex, a primary amine, and a chiral phosphoric acid allows the reaction to tolerate a wide scope of α,α-disubstituted aldehydes and alkynes, affording the corresponding allylation products in high yields and with excellent levels of enantioselectivity.

Direct asymmetric α-allylation of α-branched aldehydes by two catalytic systems with an achiral Pd complex and a chiral primary α-amino acid

Direct α-allylation of α-branched aldehydes was successfully carried out with a readily available allyl ester by combined use of two catalytic systems: Tsuji-Trost allylation reaction with an achiral palladium complex and enamine catalysis with a chiral primary α-amino acid. A quaternary carbon stereogenic center was constructed stereoselectively to give various 2,2-disubstituted pent-4-enals in good yields with high enantioselectivity.

Direct asymmetric α-allylation of aldehydes with simple allylic alcohols enabled by the concerted action of three different catalysts

Triple catalysis: The title reaction between α-branched aldehydes and allylic alcohols, which generates all-carbon quaternary stereogenic centers, constitutes the first asymmetric Tsuji-Trost-type α-allylation of carbonyl compounds with allylic alcohol (s

Enantioselective construction of quaternary stereogenic centers from tertiary boronic esters: Methodology and applications

Pin it down: A range of substrates that bear versatile functional groups with quaternary stereogenic centers have been prepared with very high enantioselectivity from tertiary boronic esters (see scheme; Cb=N,N-diisopropylcarbamoyl, pin=pinacolato). The preparation of allylboronic esters bearing contiguous quaternary and tertiary stereogenic centers, and applications to natural product synthesis are also reported.

Chiral counteranions in asymmetric transition-metal catalysis: Highly enantioselective Pd/Bronsted acid-catalyzed direct α-allylation of aldehydes

We have developed a highly enantioselective Pd/chiral acid-catalyzed α-allylation of α-branched aldehydes with an allyl amine as the allylating species that creates all-carbon quaternary stereogenic centers in high yields and enantioselectivities. To our knowledge, this is the first time that a chiral anionic ligand is applied for achieving asymmetric induction in a palladium-catalyzed allylic alkylation reaction. Copyright

The palladium-catalyzed asymmetric α-allylations of carbonyl compounds with chiral allyl esters via enamines and imines

A novel and excellent method for asymmetric α-allylation of carbonyl compounds via their chiral enamines or imines bearing allyl esters has been developed. Readily available chiral allyl esters having chirality at the α- position of the ester carbonyl group, such as (S)-proline and other (S)-α- amino acid allyl esters, have been found to serve as good asymmetric allylating reagents in palladium-catalyzed reactions of the chiral enamines and imines derived from them. The use of (S)-proline or (S)-valine allyl esters as the amino parts in the enamines or imines provided the highest optical yields of the corresponding α-allyl carbonyl compounds. A mechanism for asymmetric induction is proposed based on the stereochemical results obtained.