96853-34-8

Upstream product

• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 75-52-5 nitromethane 

Downstream Products

• 1367053-99-3 (R)-7-methoxy-4-(nitromethyl)-2-phenyl-4H-chromene-3-carbaldehyde 
• 1392824-52-0 (3aS,9R,9aS)-ethyl 3a-hydroxy-6-methoxy-9-(nitromethyl)-1,2,3,3a,9,9a-hexahydrocyclopenta[b]chromene-9acarboxylate 
• 1392824-51-9 (S)-ethyl 1-[(R)-1-(2-hydroxy-4-methoxyphenyl)-2-nitroethyl]-2-oxocyclopentanecarboxylate 
• 96853-39-3 5-Methoxy-2-(2-nitro-ethyl)-phenol 

Relevant academic research and scientific papers

Regio- and Stereoselective Cascade of β,γ-Unsaturated Ketones by Dipeptided Phosphonium Salt Catalysis: Stereospecific Construction of Dihydrofuro-Fused [2,3-b] Skeletons

Chiral (dihydro)furo-fused heterocycles are significant structural motifs in numerous natural products, functional materials and pharmaceuticals. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we develop an effective, modular method by a dipeptide-phosphonium salt-catalyzed regio- and stereoselective cascade reaction of readily available linear β,γ-unsaturated ketones with aromatic alkenes, affording a wide variety of structurally fused heterocyclic molecules in high yields with excellent stereoselectivities. Moreover, mechanistic investigations revealed that the bifunctional phosphonium salt controlled the regio- and stereoselectivities of this cascade reaction, particularly proceeding through the initial ketone α-addition followed by O-participated substitution; and the multiple hydrogen-bonding interactions between Br?nsted acid moieties of catalyst and nitro group of aromatic alkene were crucial in asymmetric induction. Given the generality, versatility, and high efficiency of this method, we anticipate that it will have broad synthetic utilities.

Phosphine-Catalyzed Enantioselective Dearomative [3+2]-Cycloaddition of 3-Nitroindoles and 2-Nitrobenzofurans

Over the past years, the metal-catalyzed dearomative cycloaddition of 3-nitroindoles and 2-nitrobenzofurans have emerged as a powerful protocol to construct chiral fused heterocyclic rings. However, organocatalytic dearomative reaction of these two classe

Facile synthesis of chiral [2,3]-fused hydrobenzofuran: Via asymmetric Cu(i)-catalyzed dearomative 1,3-dipolar cycloaddition

Intermolecular asymmetric dearomative 1,3-dipolar cycloaddition of 2-nitrobenzofurans with azomethine ylides was enabled by using a chiral Cu(i)/(S,Sp)-iPr-Phosferrox catalyst. As a result, a series of highly stereoselective chiral [2,3]-fused hydrobenzofurans possessing four contiguous stereogenic centers were obtained with good to high yields, diastereoselectivities and enantioselectivities. The reaction has broad substrate scope tolerating various functional groups.

Enantioselective dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman carbonates

The phosphine-catalyzed asymmetric dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman (MBH) carbonates or allenoate was developed. The reaction with MBH carbonates resulted in a series of cyclopentabenzofurans containing three contiguous stereocenters with good to high yields, diastereoselectivities and enantioselectivities. The use of allenoate also gave the target product with moderate enantioselectivity.

Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic Centers and an Approach to Aflatoxin Analogues

A domino reaction with the organocatalytic enantioselective Michael-acetalization-Henry reaction of 2-hydroxynitrostyrene and 5-oxohexanal was developed for the synthesis of hexahydro-6H-benzo[c]chromenones with four consecutive stereogenic centers and high enantioselectivity (up to >99% ee). The transformation of a NaBH4-reduced adduct to the aflatoxin system via the Nef-cyclization process was achieved by the assistant of ZnBr2.

Palladium-Catalyzed Highly Stereoselective Dearomative [3 + 2] Cycloaddition of Nitrobenzofurans

Stereoselective construction of highly functionalized heterocyclic molecules is an ongoing concern for the chemical community. Among the various strategies developed with this goal, catalytic asymmetric dearomatization, an attractive method for constucting cyclic molecules with multiple stereocenters from readily available aromatic compounds, has received extensive attention in recent years. Here, we report a highly stereoselective construction of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes via palladium-catalyzed dearomative [3 + 2] cycloaddition of nitrobenzofurans and nitrobenzothiophenes, respectively. Good to excellent yields (63%–92%), diastereoselectivity (13/1 → >20/1 dr), and enantioselectivity (75%–95% ee) were obtained, leading to products with vicinal stereogenic carbon centers. The reaction features wide substrate scope and diverse transformations of the products.

Sequential combination of Michael and acetalization reactions: Direct catalytic asymmetric synthesis of functionalized 4-nitromethyl-chromans as drug intermediates

Functionalized chiral 4-nitromethyl-chromans as drug intermediates were achieved for the first time through sequential combination of Michael and acetalization reactions on 2-(2-nitro-vinyl)-phenols with acetone and alcohols in the presence of a catalytic

A new efficient method for the total synthesis of linear furocoumarins

A new efficient method for the synthesis of linear furocoumarins by a Nef reaction and intramolecular cyclocondensation in one pot results in the construction of a benzofuran ring. This method provides a new strategy to furnish the benzofuran framework easily, and also allows the convenient synthesis of furocoumarin derivatives with different substituents on the coumarin ring by a subsequent Pechmann reaction. This strategy has also been applied to the preparation of four additional benzofuran derivatives. Georg Thieme Verlag Stuttgart.