84620-27-9

Upstream product

• 2198-64-3 N-benzoyl-L-alanine 
• 13302-43-7 (S)-2-phenyl-4-methyl-5(4H)-oxazolone 
• 106-95-6 allyl bromide 
• 886466-65-5 5-allyloxycarbonyloxy-4-methyl-2-phenyloxazole 
• 98-88-4 benzoyl chloride 
• 53777-87-0 N-benzoyl-alanine allyl ester 
• 5162-44-7 1-bromo-4-butene 
• 51127-13-0 2-phenyl-4-methyl-4H-oxazolin-5-one 
• 114234-15-0 N-<1-(N,N-Dimethylcarbamoyl)-1-methylbut-3-enyl>benzamid 
• 65-85-0 benzoic acid 
• 107267-46-9 2-Allyl-3-(dimethylamino)-2-methyl-2H-azirin 
• 84537-31-5 2-phenyl-4-methyl-4-(3-methyl-2-butenyl)-Δ²-oxazolin-5-one 
• 2198-64-3 N-Benzoylalanine 

Downstream Products

• 160281-26-5 N-Benzoyl-(S)-α-(2-propenyl)-α-alanine 
• 96886-55-4 (S)-α-allylalanine 
• 46181-30-0 6-methyl-2-phenylpyridine 
• 51127-13-0 2-phenyl-4-methyl-4H-oxazolin-5-one 
• 56434-99-2 2-methyl-6-phenyl-pyridine; picrate 
• 84537-31-5 2-phenyl-4-methyl-4-(3-methyl-2-butenyl)-Δ²-oxazolin-5-one 
• 84537-32-6 2-phenyl-2-(1,1-dimethyl-2-propenyl)-4-methyl-Δ³-oxazolin-5-one 

Relevant academic research and scientific papers

Palladium-catalyzed asymmetric decarboxylative allylation of azlactone enol carbonates: Fast access to enantioenriched α-allyl quaternary amino acids

We report a fast protocol for the synthesis of enantioenriched quaternary 4-allyl oxazol-5-ones. The key step is a Pd-catalyzed enantioselective Tsuji allylation of azlactone allyl enol carbonates, which can be easily prepared starting from racemic α-amino acids. The use of (R,R)-DACH-phenyl Trost chiral ligand allowed the attainment of the allylated derivatives in very good yields (83–98 %) and with ee up to 85 %. Scaling up the allylation protocol to gram quantities did not affect the yields end ee values. The produced 4-allyl azlactones can be converted into the corresponding quaternary amino acids or submitted to further synthetic elaborations exploiting the allyl moiety as a handle for the attachment of alkyl and aryl groups. After hydrolysis of the azlactone ring, the zwitterionic amino acids can be attained in enantiopure or nearly optically pure form through only one recrystallization step.

BEMP-promoted C(4)-alkylation of 4-alkyloxazol-5(4 H)-ones: A rapid and efficient route to α,α-dialkyl-α-amino acids

Rapid and efficient C(4)-alkylation of 4-alkyloxazol-5(4H)-ones has been achieved by the utilization of BEMP as base. 4,4-Dialkyloxazol-5(4H)-ones, which can easily be hydrolyzed into free α,α-dialkyl-α-amino acids, were obtained in high yields (up to 99%

Enantioselective quaternization of 4-substituted oxazol-5-(4H)-ones using recoverable Cinchona-derived dimeric ammonium salts as phase-transfer organocatalysts

Dimeric anthracenyldimethyl-derived Cinchona ammonium salts are used as chiral organocatalysts (5 mol %) for the enantioselective 4-alkylation of 4-substituted azlactones. The corresponding adducts bearing a new quaternary center were obtained with up to

Enantioselective decarboxylative alkylation reactions: Catalyst development, substrate scope, and mechanistic studies

α-Quaternary ketones are accessed through novel enantioselective alkylations of allyl and propargyl electrophiles by unstabilized prochiral enolate nucleophiles in the presence of palladium complexes with various phosphinooxazoline (PHOX) ligands. Excellent yields and high enantiomeric excesses are obtained from three classes of enolate precursor: enol carbonates, enol silanes, and racemic β-ketoesters. Each of these substrate classes functions with nearly identical efficiency in terms of yield and enantioselectivity. Catalyst discovery and development, the optimization of reaction conditions, the exploration of reaction scope, and applications in target-directed synthesis are reported. Experimental observations suggest that these alkylation reactions occur through an unusual inner-sphere mechanism involving binding of the prochiral enolate nucleophile directly to the palladium center. Sly as a PHOX: The development of an enantioselective decarboxylative palladium-catalyzed allylic alkylation reaction, utilizing phosphinooxazoline ligands, is described. The catalyst is applied to a range of allyl enol carbonate, silyl enol ether, and allyl β-ketoester substrates to provide alkylated ketone products in excellent yield and good ee (see scheme). The utility of these products is demonstrated by their use in several asymmetric syntheses. Mechanistic studies are reported suggesting an unusual inner-sphere mechanism. Copyright

Formation of Methyl 5,6-Dihydro-1,3(4H)-thiazine-4-carboxylates from 4-Allyl-1,3-thiazol-5(4H)-ones

The reaction of N-benzamid (1) with HCl or TsOH in MeCN or toluene yields a mixture of 4-allyl-4-methyl-2-phenyl-1,3-thiazol-5(4H)-one (5a) and allyl 4-methyl-2-phenyl-1,3-thiazol-2-yl sulfide (11; Scheme

2,4-Bis(4-methylphenylthio)-1,3,2λ5,4λ5-dithiadiphosphetane-2,4-dithione: A New Reagent for Thiation of N,N-Disubstituted Amides

As a new reagent for the thiation of amides, the easily accessible 2,4-bis(4-methylphenylthio)-1,3,2λ5,4λ5-dithiadiphosphetane-2,4-dithione (9) shows a remarkable selectivity.This selectivity - the preferred thiation of N,N-disubstituted amides - is complementary to the one of the well known Lawesson reagent.Thiation of diamides of type 2 with 9 leads via cyclization of the corresponding dithiodiamides directly to 1,3-thiazole-5(4H)-thiones 1.

Aza Cope Rearrangements in the Cyclopropenyl-and Allyl-Substituted Δ2-Oxazolinone Systems

The scope of the thermal and photochemical reorganization reactions of a number of cyclopropenyl- and allyl- substituted oxazolinones has been examined.These systems undergo a facile sigmatropic rearrangement in accord with orbital symmetry predictions. 2-Methyl-4-allyl-Δ2-oxazolinones were found to undergo a 3,3-sigmatropic allyl shift on thermolysis to give the Δ3-oxazolinone isomer.In contrast, on direct irradiation the 2-methyl-4-allyl-Δ3-oxazolinones undergo a 1,3-allyl shift to give the Δ2-isomer.The 4,4-disubstituted Δ2-oxazolinones undergo decarbonylat ion either on irradiation or by flash vacuum pyrolysis to give acetimides.The acetimides formed were easily hydrolyzed to give the corresponding ketones.The excited-state behavior of the 2-phenyl-4-methyl-Δ2-oxazolinone system was found to be markedly different from that encountered with the 2-methyl-4-phenyl-substituted isomer.The rationale for the difference in behavior is discussed.