60208-56-2

Upstream product

• 16704-20-4 (E)-(prop-1-ene-1,3-diyl-3-deuterio)dibenzene 
• 611-71-2 (R)-Mandelic Acid 
• 20698-91-3 (R)-methyl mandelate 
• 103-82-2 phenylacetic acid 
• 31491-21-1 2-phenyl-1,1-bis(trimethylsilyloxy)ethene 
• 106137-98-8 (R)-(E)-1,3-diphenyl-3-trimethylsilylpropene 
• 286967-46-2 2-methoxy-2-methyl-4-phenyl-1,3-dioxolane 
• 39904-21-7 2-methoxy-2-methyl-4-phenyl-1,3-dioxolane 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 33942-00-6 (S)-(-)-2-chloro-2-phenethylacetic acid 

Downstream Products

• 60168-73-2 R-(+)-2-d₁-phenylethanol methanesulfonate 
• 78601-59-9 (R)-(+)-2-d₁-phenylethyl bromide 
• 10606-76-5 (R)-2-phenylethyl 4-methylbenzenesulfonate 
• 286967-49-5 1-trimethylsilyloxy-3(S)-[2-deutero-2(R)-phenethyl]-5(R)-methyl-1-cyclohexene 
• 60168-60-7 (S)-cis-1-Deuterio-1-phenyl-4-methyl-2-penten 
• 68566-80-3 (S)-(+)-1-phenylethane-1-d₁ 

Relevant academic research and scientific papers

Deracemizing α-Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis-Silyl Ketene Acetals with Water or Methanol

We report a highly enantioselective catalytic protonation of bis-silyl ketene acetals. Our method delivers α-branched carboxylic acids, including nonsteroidal anti-inflammatory arylpropionic acids such as Ibuprofen, in high enantiomeric purity and high yields. The process can be incorporated in an overall deracemization of α-branched carboxylic acids, involving a double deprotonation and silylation followed by the catalytic asymmetric protonation.

9-Borabicyclo[3.3.2]decanes and the asymmetric hydroboration of 1,1-disubstituted alkenes

The syntheses of the optically pure asymmetric hydroborating agents 1 (a, R = Ph; b, R = TMS) in both enantiomeric forms are reported. These reagents are effective for the hydroboration of cis-, trans- and trisubstituted alkenes. More significantly, they exhibit unprecedented levels of selectivity in the asymmetric hydroboration of 1,1-disubstituted alkenes (28-92% ee), a previously unanswered challenge in the nearly 50 year history of this reagent-controlled process. For example, the hydroboration of α-methylstyrene with 1a produces the corresponding alcohol 6f in 78% ee (cf., Ipc2BH, 5% ee). Suzuki coupling of the intermediate adducts 5 produces the nonracemic products 7 very effectively (50-84%) without loss of optical purity. 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.

ANTI STEREOCHEMISTRY IN PROTODESILYLATION OF AN OPTICALLY ACTIVE ALLYLSILANE WITH TRRIFLUOROACETIC ACID-D

SE' reaction of (R)-(E)-1,3-diphenyl-3-trimethylsilylpropene with trifluoroacetic acid-d proceeded with anti stereochemistry to give (R)-(E)-1,3-diphenylpropene-3-d.