134273-10-2

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 30076-98-3 (3,3-dimethoxypropyl)benzene 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 57213-25-9 2-(1-Hydroxy-3-phenyl-propyl)-cyclopentanone 
• 933-06-2 1-acetoxycyclopentene 
• 120-92-3 cyclopentanone 
• 30842-23-0 cyclopent-1-en-1-yl diethyl phosphate 

Relevant academic research and scientific papers

RuPHOX-Ru-Catalyzed Selective Asymmetric Hydrogenation of Exocyclic α,β-Unsaturated Pentanones

A RuPHOX-Ru catalyzed selective asymmetric hydrogenation of exocyclic α,β-unsaturated ketones has been developed, furnishing the corresponding chiral exocyclic allylic alcohols in high yields and with up to >99.5percent ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 10000 S/C) without any loss in reaction activity and enantioselectivity. The resulting hydrogenated products could be easily transformed to several biologically active compounds with high asymmetric performance. The asymmetric protocol provides an efficient methodology for the synthesis of chiral exocyclic allylic alcohols.

Installation of a chiral side chain to a 2-alkylidene-1-cycloalkan-1-ol unit by using allylic substitution

The allylic substitution of optically active exocyclic allylic esters of cyclopentane and cyclohexane with ArMgBr-based copper reagents (Ar = aryl) was examined. ArMgBr/Cu(acac)2 in a 2:1 ratio was an adequate reagent to produce the anti-SN2' products efficiently in terms of regioselectivity (95-99a€‰%), chirality transfer (91-99a€‰%), and yield (71-91a€‰%). The Ar groups that were successfully installed include Ph and p-tolyl, those with electron-donating (i.e., p-MeOC6H4) and electron-withdrawing groups (i.e., p-FC6H4), and those with sterically demanding groups (i.e., o-tolyl, o-MeOC6H 4). In an examination of an alkyl reagent, BuMgBr/CuBr·Me 2S in a 2:1 ratio in the presence of ZnI2 afforded the product with high regioselectivity (99a€‰%) and in good yield (91a€‰%). The allylic substitution of exocyclic allylic picolinates (n = 1, 2; R = Ph(CH2)2, iPr, Ph) with a ArCu(acac)MgBr reagent (Ar = Ph, p-tolyl, p-MeOC6H4, p-FC6H4, o-tolyl, o-MeOC6H4) that was derived from a 2:1 ratio of ArMgBr and Cu(acac)2 efficiently afforded the anti-SN2' products in terms of regioselectivity (95-99a€‰%), chirality transfer (91-99a€‰%), and yield (71-91a€‰%). Copyright

RADICAL β-FRAGMENTATION OF BICYCLOCARBINOLAMIDES: SYNTHESIS OF FIVE- AND EIGHT-MEMBERED CYCLIC IMIDES

The influence of 4-alkyl or 4-aryl substituents in the regioselectivity of the β-fragmentation of carbinolamidyl radicals generated from the corresponding carbinolamides (7-13) by irradiation with visible light in the presence of (diacetoxyiodo)benzene an

The Reactions of Acetals with Silyl Enol Ethers Promoted by the Combination of Tin(II) Chloride and Organic Halide. Novel and Convenient Synthesis of α,β-Unsaturated Ketones

Acetals react with silyl enol ethers to give condensation products in good yield by the action of a reactive halide such as acetyl chloride or methoxymethyl chloride along with a catalytic amount of SnCl2.The procedure employing excessive amount of halide offers a novel and convenient method to synthesize conjugated enones.

Anodic Oxidation of Triphenylphosphine in the Presence of Enol Silyl Ethers or Enol Esters. Electrochemical One-step Preparation of 2-Oxocycloalkyltriphenylphosphonium Tetrafluoroborates

Electrochemical oxidation of triphenylphosphine in the presence of cyclic enol silyl ethers or enol esters gave 2-oxocycloalkyltriphenylphosphonium salts, which underwent the Wittig reaction with aldehydes to afford (E)-2-alkylidenecycloalkan-1-ones.