87352-05-4

Basic information

• Product Name: 3-Azetidinecarboxylic acid, 1-(1,1-dimethylethyl)-2-oxo-4-phenyl-, methyl ester, trans-
• CAS NO: 87352-05-4
• Molecular Formula: C15H19NO3
• Molecular Weight: 261.321
• Mol File: 87352-05-4.mol

Chemical Properties

• CAS DataBase Reference: 3-Azetidinecarboxylic acid, 1-(1,1-dimethylethyl)-2-oxo-4-phenyl-, methyl ester, trans-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Azetidinecarboxylic acid, 1-(1,1-dimethylethyl)-2-oxo-4-phenyl-, methyl ester, trans-(87352-05-4)
• EPA Substance Registry System: 3-Azetidinecarboxylic acid, 1-(1,1-dimethylethyl)-2-oxo-4-phenyl-, methyl ester, trans-(87352-05-4)

Safety Data

• Hazardous Substances Data: 87352-05-4(Hazardous Substances Data)

Upstream product

• 162517-76-2 N-benzyl-N-tert-butyl-α-(methoxycarbonyl)-α-diazoacetamide 
• 3378-72-1 N-tert-butylbenzylamine 
• 1010785-89-3 C₁₅H₂₁O₃N 
• 87190-61-2 trans-N-tert-Butyl-4-carbomethoxy-3-phenyl-trans-5-nitroisoxazolidine 

Relevant articles and documents

Site Selectivity in Pd-Catalyzed Reactions of α-Diazo-α-(methoxycarbonyl)acetamides: Effects of catalysts and substrate substitution in the synthesis of oxindoles and β-lactams

The Pd-catalyzed intramolecular carbene C–H insertion of α-diazo-α(methoxycarbonyl)acetamides to prepare oxindoles as well as β-lactams was studied. In order to identify what factors influence the selectivity of the processes, we explored how the reactions are affected by the catalyst type, using two oxidation states of Pd and a variety of ligands. It was found that, in the synthesis of oxindoles, ((IMes)Pd(NQ))2 can be used as an alternative to Pd2(dba)3 to catalyze the carbene CArsp2–H insertion, although it was less versatile. On the other hand, it was demonstrated that the Csp3–H insertion leading to β-lactams can be effectively promoted by both Pd(0) and Pd(II) catalysts, the latter being most efficient. Insight into the reaction mechanisms involved in these transformations was provided by DFT calculations.

Palladium Catalysis in the Intramolecular Carbene C–H Insertion of α-Diazo-α-(methoxycarbonyl)acetamides to Form β-Lactams

The intramolecular carbene C–H insertion of α-diazo-α-(methoxycarbonyl)acetamides leading to β-lactams is effectively catalyzed by palladium complexes. It is found that although Pd0 catalysts typically produce mixtures of β-lactams together wit

Ruthenium- and rhodium-catalyzed carbenoid reactions of diazoesters in hexaalkylguanidinium-based ionic liquids

Hexaalkylguanidinium-based room-temperature ionic liquids were investigated as solvents for the cyclopropanation of styrene with diazoacetates catalyzed by Rh2(OAc)4 or [Ru2(μ-OAc) 2(CO)4]n. While the yields of the formed cyclopropanes are much lower compared to the reactions performed in dichloromethane, the diastereomeric ratio is not significantly affected by the change of the reaction medium. Immobilization of the catalysts is only partially successful. In contrast to this intermolecular reaction, the Ru-catalyzed formation of a β-lactam by an intramolecular carbenoid C-H insertion of an α-methoxycarbonyl-α-diazoacetamide occurs in high yield, similar to the Rh2(OAc)4-catalyzed reaction. The cis → trans isomerization of the resulting 1-tert-butyl-3-methoxycarbonyl-4-phenyl-azetidin- 2-one is accelerated in the ionic liquid N,N-dibutyl-N',N'-diethyl-N'',N''- dihexylguanidin-ium triflate.

Ruthenium catalysts for carbenoid intramolecular C-H insertion of 2-diazoacetoacetamides and diazomalonic ester amides

The intramolecular carbenoid C-H insertion of 2-diazoacetoacetamides, leading to γ- and/or β-lactams, is catalyzed effectively by dinuclear Ru(I,I) complexes of the type [Ru2(μ-L1)2(CO)4L22], where L1 is a bidentate bridging acetate, calix[4]arenedicarboxylate, saccharinate or 6-chloropyridin-2-olate ligand. By comparison with rhodium catalysts, namely dirhodium tetraacetate and dirhodium calix[4]arenedicarboxylate complexes, product yields are similarly high and the regioselectivity of the insertion reaction is the same. Surprisingly, even the ruthenium(0) cluster Ru3(CO)12 was found to be an effective catalyst for carbenoid C-H insertion of 2-diazoacetoacetamides and also of some diazoacetamides. In terms of diastereoselectivity, trans-isomers of β- and γ-lactams are obtained. However, the β-lactam obtained from diazomalonic ester amide 2 yields the cis-isomer stereoselectively, which slowly rearranges to the trans-isomer.

New Synthesis of β-Lactams Based on Nitrone Cycloaddition to Nitroalkenes

Heating a sample of the major 5-nitro-substituted isoxazolidine isomer obtained from the reaction of a C-phenyl-N-alkylnitrone with trans-1-cyano-2-nitroethylene in methanol resulted in ring contraction and formation of 4-phenyl-3-cyano-N-alkyl-2-azetidin