16123-41-4

Upstream product

• 2398-37-0 3-methoxyphenyl bromide 
• 563-47-3 3-Chloro-2-methylpropene 
• 383877-64-3 3-(3-methoxyphenyl)-2-methylacrylaldehyde 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 7757-83-7 sodium sulfite 

Relevant academic research and scientific papers

Highly pH-Dependent Chemoselective Transfer Hydrogenation of α,β-Unsaturated Aldehydes in Water

The pH-dependent selective Ir-catalyzed hydrogenation of α,β-unsaturated aldehydes was realized in water. Using HCOOH as the hydride donor at low pH, the unsaturated alcohol products were obtained exclusively, while the saturated alcohol products were formed preferentially by employing HCOONa as the hydride donor at high pH. A wide range of functional groups including electron-rich as well as electron-poor substituents on the aryl group of α,β-unsaturated aldehydes can be tolerated, affording the corresponding products in excellent yields with high TOF values. High selectivity and yields were also observed for α,β-unsaturated aldehydes with aliphatic substituents. Our mechanistic investigations indicate that the pH value is critical to the chemoselectivity.

Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates

Nickel-catalyzed enantioselective cross-couplings between symmetric cyclic sulfates and aromatic Grignard reagents are described. These reactions are effective with a broad range of substituted cyclic sulfates and deliver products with asymmetric tertiary carbon centers. Mechanistic experiments point to a stereoinvertive SN2-like oxidative addition of a nickel complex to the electrophilic substrate.

Cyclization substrates and 7α-substituted 19-norsteroid derivatives

Novel cyclization substrates are disclosed of the formula STR1 wherein: (a) R1 is H or alkyl of one to four carbon atoms; (b) R2 is H or alkyl of one to four carbon atoms, with the proviso that R1 is H when R2 is alkyl, and with the proviso that R2 is H when R1 is alkyl; (c) R3 is a leaving group selected from the group consisting of hydroxy, alkoxy of one to four carbons, alkoxyalkoxy of two to four carbons, acyloxy of one to about seven carbons, and trialkylsilyloxy of less than fifteen carbons; (d) R4 is hydrocarbyl of one to four carbon atoms, a hydrocarbyl of one to two carbon atoms substituted by halogen or alkoxy of one to two carbons, or alkoxy of one to four carbon atoms; and (e) R5 and R5 ' each are H, OH, alkyl, trialkylsilyloxy, or an esterified or etherified hydroxy-group of about one to ten carbon atoms. A method is disclosed for the cyclization of the compounds of formula III leading to novel and biologically active compounds of the following formulae: STR2 having R1 through R5 ' as defined above, with R6 being alkyl of from one to about four carbon atoms, among which are intermediates for preparing well-known biologically active 7α-substituted steroids, such as 7α-methyl-oestrone; 7α-methoxy-oestradiol and the like.