35039-72-6

Usage

InChI:InChI=1/C16H15NO3/c18-14(11-12-7-3-1-4-8-12)17-15(16(19)20)13-9-5-2-6-10-13/h1-10,15H,11H2,(H,17,18)(H,19,20)

Upstream product

• 56674-25-0 2-hydroxy-2-(2-phenylacetamido)acetic acid 
• 71-43-2 benzene 
• 171181-53-6 methyl N^α-(diphenylmethylene)-DL-phenylglycinate 
• 24461-61-8 phenylglycine methyl ester 
• 2835-06-5 phenylglycin 
• 103-80-0 phenylacetyl chloride 
• 103-81-1 Benzeneacetamide 

Downstream Products

• 60050-57-9 2-benzyl-4-phenyl-4H-oxazolin-5-one 
• 63069-08-9 N-(3-cyclohexyl-2-cyclohexylimino-4-oxo-5-phenyl-oxazolidin-5-yl)-2-phenyl-acetamide 

Relevant academic research and scientific papers

Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and γ-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.

Regioselective synthesis of tetrasubstituted pyrroles by 1,3-dipolar cycloaddition and spontaneous decarboxylation

We developed a novel regioselective synthesis of tetrasubstituted pyrroles via the classic 1,3-dipolar cycloaddition of α,β-unsaturated benzofuran-3(2H)-one and azlactones (1) followed by spontaneous decarboxylation. The complete regiochemical control of tetrasubstituted pyrroles was confirmed by the orthogonal synthesis of complementary regioisomers (7a and 7b) simply by using different azlactones (1a and 1b, respectively).

INTRA VS INTERMOLECULAR AMIDOALKILATION OF AROMATICS

Three tipes of intramolecular amidoalkylation reactions of aromatics, two endotrigonal and one exotrigonal (I, II, III), leading to indolone, N-acylisoquinolines, isoquinolone and benzazepinone derivatives were studied.In the presence of external aromatic nucleophiles competing intermolecular amidoalkylations were observed (1->2, 13->14).The mechanism and the synthetic limitations of the three types of cyclization is discussed.

INTER VS INTRAMOLECULAR AMIDOALKYLATIONS OF AROMATICS - A NEW SYNTHESIS OF OXINDOLES, ISOQUINOLONES AND BENZAZEPINONES

A new synthesis of oxindoles (8) isoquinolones (5) and benzazepinones (10) by the intramolecular amidoalkylation of aromatic amides of bismethoxycarbonylaminoacetic acid (4, 7, 9) is described.