61845-91-8

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 103-49-1 dibenzylamine 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 

Downstream Products

• 1643654-91-4 (2S,3S)-2-acetyl-N,N-dibenzyl-4-nitro-3-phenylbutanamide 
• 118522-21-7 N,N-dibenzyl-α-diazoacetamide 
• 88121-67-9 (3S,4S)-3-Acetyl-1-benzyl-4-phenyl-azetidin-2-one 
• 134568-13-1 4-(N,N-Dibenzylcarbamoyl)-3-hydroxy-5-methyliden-2(5H)-furanon 

Relevant academic research and scientific papers

Direct Carboxylation of the Diazo Group ipso-C(sp2)-H bond with Carbon Dioxide: Access to Unsymmetrical Diazomalonates and Derivatives

The direct carboxylation of the ipso-C(sp2)-H bond of a diazo compound with carbon dioxide under mild reaction conditions is described. This method is transition-metal-free, uses a weak base, and proceeds at ambient temperature under atmospheric pressure in carbon dioxide. The carboxylation exhibits high reactivity and is amenable to subsequent diversification. A series of unsymmetrical 1,3-diester/keto/amide diazo compounds are obtained with moderate to excellent yields (up to 99%) with good functional group compatibility.

Diazo- And transition-metal-free C-H insertion: A direct synthesis of β-lactams

Carbene intermediates are very useful species for a range of reactions including C-H insertions and cycloadditions. They are most commonly generated by metal-catalyzed release of nitrogen gas from diazo precursors. Herein, we present a novel C-H insertion

In situ-generated iodonium ylides as safe carbene precursors for the chemoselective intramolecular buchner reaction

A chemoselective intramolecular Buchner reaction employing iodonium ylides as safe carbene precursors has been developed. Iodonium ylides are generated in situ from N-benzyl-2-cyanoacetamides and PhI(OAc)2 in the presence of base and undergo intramolecular Buchner reaction under catalysis from Cu(OAc)2·H2O, affording fused cyclohepta-1,3,5-triene derivatives in up to 85% yield. The N,N-dibenzyl-2-cyanoacetamides with two different benzyl groups undergo intramolecular Buchner reaction on their electron-rich benzyl groups selectively. The reaction is not sensitive to air and moisture and uses a safe alternative version of the corresponding diazo starting materials. The overall transformation involving the carbene pathway has been verified.

Organocatalytic enantio- and diastereoselective conjugate addition to nitroolefins: When ketoamides surpass ketoesters

Our findings on the bifunctional squaramide-catalyzed enantioselective conjugate addition of ketoamides to nitroolefins are disclosed. It appears that simple acyclic methylene ketoamides, unlike the extensively studied ketoesters, afford the products in excellent diastereoselectivities, and maintain high yields and enantioselectivities. Moreover, competition and kinetic studies were conducted to rationalize the observed reactivity and selectivity. The high level of diastereocontrol, along with the amenability of the amide group to postfunctionalization, dramatically increase the synthetic usefulness of the transformation.

AN INTRAMOLECULAR DIELS-ALDER REACTION OF A Z-DIENE. GENERATION OF THE CHIRAL ISOINDOLONE NUCLEUS OF CYTOCHALASIN C.

Aldol/elimination reactions of β-ketoamides with methyl glyoxylate result in highly selective production of Z-α, β-unsaturated amides.An intramolecular Diels-Alder reaction of a triply activated dienophile derived from chiral dienylamine 7ZE stereospecifically affords chiral bicyclic lactam 11 at room temperature.