89398-25-4

Upstream product

• 1044771-26-7 4(S)-2-methoxy-2-methyl-4-phenyl-1,3-dioxolane 
• 103590-74-5 (R)-(+)-2-chloro-2-phenethylacetic acid 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 21210-43-5 (S)-Methyl mandelate 
• 17199-29-0 (S)-Mandelic acid 
• 10606-75-4 (S)-2-Phenyl<2-²H₁>ethanol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 71698-86-7 (R)-(-)-1-deuterioethylbenzene 
• 883236-68-8 N-p-toluenesulfonyl-2-(2-phenylethyl)-3-pyrroline 
• 286967-48-4 (S)-(-)-2-d₁-phenethyl bromide 
• 1414335-87-7 C₂₆H₂₃⁽²⁾HP⁽¹⁺⁾*Br^(1-) 

Relevant academic research and scientific papers

Enantioconvergent Amination of Racemic Tertiary C-H Bonds

Racemization is considered to be an intrinsic stereochemical feature of free radical chemistry as can be seen in traditional radical halogenation reactions of optically active tertiary C-H bonds. If the facile process of radical racemization could be effe

Reconciling the stereochemical course of nucleopalladation with the development of enantioselective wacker-type cyclizations

A stereochemical substrate probe was used to assess the factors that affect the stereochemical course of nucleopalladation in the context of an enantioselective Wacker-type reaction. The enantioselectivity correlates directly with the nucleopalladation pathway, and both the neutral-donor and anionic ligands on palladium are capable of controlling selectivity for cis- or trans-nucleopalladation (see scheme; TFA=trifluoroacetate). Copyright

Stereochemical Dynamics of Aliphatic Hydroxylation by Cytochrome P-450

Previous studies on the stereochemistry of hydroxylation by cytochrome P-450 enzymes have been contradictory and confusing.Therefore, the hydroxylation of four isotopically substituted phenylethane substrates has been examined with a single isozyme of rabbit liver microsomal cytochrome P-450.In each case the corresponding 1-phenylethanol was essentially the only product.With ordinary phenylethane, the product was 48percent R-1-phenylethanol and 52percent the S isomer.With (R)-phenylethane-1-d, the product was 42percent R alcohol, while with (S)-phenylethane-1-d the product was 70percent R alcohol.When the substrate was phenylethane-1,1-d2, 50percent R alcohol was produced.The alcohols from the single-deuterium-substituted substrates were highly enriched in deuterium, indicating the operation of a large deuterium isotope effect on hydrogen removal.Most importantly, 23-40percent of the hydroxylation events resulted in alcohol with configuration opposite to that of the original hydrocarbon substrate.These "crossover" events require the intermediacy of a discrete tricoordinate carbon intermediate.These data unambiguously demonstrate that hydroxylation stereospecificity must be enforced by the surrounding protein tertiary structure and is not an inherent feature of the cytochrome P-450 reaction mechanism.