136265-09-3

Upstream product

• 555-68-0 (E)-3-Nitrocinnamic acid 
• 623-73-4 diazoacetic acid ethyl ester 
• 99-61-6 3-nitro-benzaldehyde 
• 105-36-2 ethyl bromoacetate 
• 109-63-7 boron trifluoride diethyl etherate 

Downstream Products

• 5676-61-9 (Z)-3-(3-nitrophenyl)acrylic acid 

Relevant academic research and scientific papers

Iron(IV)-Corrole Catalyzed Stereoselective Olefination of Aldehydes with Ethyl Diazoacetate

Iron(IV)-corrole complexes were first investigated as catalysts for olefination of aldehydes with ethyl diazoacetate in the presence of triphenylphosphine. Efficient olefination of aromatic aldehydes with high trans-selectivity was observed, showing iron corrole is a new kind of promising catalyst for olefination reaction. Transformation of the phosphazine to ylide by iron(IV) corrole was proved to be the key step in the present system.

1,3-Diphenyldisiloxane Enables Additive-Free Redox Recycling Reactions and Catalysis with Triphenylphosphine

The recently reported chemoselective reduction of phosphine oxides with 1,3-diphenyldisiloxane (DPDS) has opened up the possibility of additive-free phosphine oxide reductions in catalytic systems. Herein we disclose the use of this new reducing agent as an enabler of phosphorus redox recycling in Wittig, Staudinger, and alcohol substitution reactions. DPDS was successfully utilized in ambient-temperature additive-free redox recycling variants of the Wittig olefination, Appel halogenation, and Staudinger reduction. Triphenylphosphine-promoted catalytic recycling reactions were also facilitated by DPDS. Additive-free triphenylphosphine-promoted catalytic Staudinger reductions could even be performed at ambient temperature due to the rapid nature of phosphinimine reduction, for which we characterized kinetic and thermodynamic parameters. These results demonstrate the utility of DPDS as an excellent reducing agent for the development of phosphorus redox recycling reactions.

Silver-Catalyzed Cross-Olefination of Donor and Acceptor Diazo Compounds: Use of N-Nosylhydrazones as Diazo Surrogate

The cross-olefination reaction of donor and acceptor diazo compounds was explored. The use of N-nosylhydrazones as diazo surrogates and the dependence on silver catalysis were crucial for the reaction development. A variety of (hetero)aryl N-nosylhydrazones and α-diazo esters, amides, and phosphonates were compatible, and the functionalized alkene products were afforded in good to high yields with moderate (Z)/(E) selectivities. The experimental and DFT calculation results suggest that the cross-selectivity is due to selective activation of the silver catalyst for donor diazo compounds.

BF3·OEt2-mediated: Syn -selective Meyer-Schuster rearrangement of phenoxy propargyl alcohols for Z -β-aryl-α,β-unsaturated esters

Synthesis of Z-β-aryl-α,β-unsaturated esters from readily available 1-aryl-3-phenoxy propargyl alcohols is achieved via a BF3-mediated syn-selective Meyer-Schuster rearrangement under ambient conditions. The reaction mechanism is postulated to involve an electrophilic borylation of an allene intermediate as the key step to kinetically control the stereoselectivity.

Methods of using α-phosphonosulfonate squalene synthetase inhibitors including the treatment of atherosclerosis and hypercholesterolemia

α-Phosphonosulfonate compounds are provided which inhibit the enzyme squalene synthetase and thereby inhibit cholesterol biosynthesis. These compounds have the formula STR1 wherein R2 is OR5 or R5a ; R3 and R5 are independently H, alkyl, arylalkyl, aryl or cycloalkyl; R5a is H, alkyl, arylalkyl or aryl; R4 is H, alkyl, aryl, arylalkyl, or cycloalkyl;, Z is H, halogen, lower alkyl or lower alkenyl; and R1 is a lipophilic group which contains at least 7 carbons and is alkyl, alkenyl, alkynyl, mixed alkenyl-alkynyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroarylalkyl, cycloheteroalkyl, cycloheteroalkylalkyl; as further defined above; including pharmaceutically acceptable salts and or prodrug esters of the phosphonic (phosphinic) and/or sulfonic acids.