1029317-00-7

Upstream product

• 74-88-4 methyl iodide 
• 4931-66-2 methyl 5-oxopyrrolidine-2-carboxylate 
• 824-94-2 p-methoxybenzyl chloride 
• 67-56-1 methanol 
• 1029316-95-7 C₂₀H₂₀N₄O₃ 

Downstream Products

• 1086447-58-6 1-(4-methoxybenzyl)-2-methyl-5-oxopyrrolidine-2-carbaldehyde 

Relevant academic research and scientific papers

Rhodium-Catalyzed Stereospecific C?H Amination for the Construction of Spiroaminal Cores: Reactivity Difference between Nitrenoid and Carbenoid Species against Amide Functionality

Metal nitrenoids and metal carbenoids exhibit similar reactivity for insertion into a C?H bond and a C=C double bond. These reactions have attracted the attention of organic chemists due to their unusual bond-forming ability, but the reactivity difference between these chemical species has not been studied. In this paper, we examined the reactivity difference using the corresponding Rh nitrenoid and Rh carbenoid precursors. The Rh nitrenoid inserted into an intramolecular C(sp3)?H bond adjacent to an amide nitrogen, affording functionalized spiroaminals that are ubiquitous in natural products, while the Rh carbenoid inserted into an amide C?N bond. The totally different reactivity was rationalized by the relatively low energy barrier for the C?H insertion reaction of the Rh nitrenoid. Computational analysis suggests that the origin of the discrepancy is the electrophilicity of the coordinating atoms to the Rh complex.

2-Nitrophenyl isocyanide as a versatile convertible isocyanide: Rapid access to a fused γ-lactam β-lactone bicycle

(Chemical Equation Presented) 2-Nitrophenyl isocyanide is introduced as a convertible isocyanide with demonstration of its feasibility and applicability in an efficient synthesis of the fused γ-lactam β-lactone bicycle of proteasome inhibitor omuralide. Starting from a linear keto acid precursor, the fused γ-lactam β-lactone bicycle was prepared in four steps by a sequential biscyclization strategy; a stereocontrolled Ugi reaction and the concomitant direct β-lactonization following the formation of an N-acylbenzotriazole intermediate. The N-acylbenzotriazole is amenable to intra- or intermolecular attack from a variety of nucleophiles with a catalytic amount of base to form the pyroglutamic acid derivatives.