(R,R)‐1,2‐Diphenyl‐1,2‐Ethanediol (Stilbene Diol)

McKee, Blaine H.; Gilheany, Declan G.; Sharpless, K. Barry

doi:10.1002/0471264180.os070.06

Cited by 2 publications

(2 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The subsequent chiral ligand tested in our investigation was represented by ( S,S )- or ( R,R )-1,2-diphenyl-1,2-ethanediol (stilbene diol, or hydrobenzoin, HB). This compound, which could be obtained in high enantiomeric purity by an enantioselective dihydroxylation, is currently commercially available. Diols structurally related to HB had been used as ligands in a hydroperoxide oxidation of sulfide, catalyzed by a stoichiometric amount of a titanium complex (55−81% yields, 43−84% ee).…”

Section: Resultsmentioning

confidence: 99%

A Straightforward Enantioselective Route to Dialkyl Sulfoxides Based upon Two Carbon-for-Carbon Substitution Reactions on the Sulfinyl Group

et al. 2002

View full text Add to dashboard Cite

Benzyl p-bromophenyl sulfoxide 1 was obtained on a multigram scale and in an enantiomerically pure form by an enantioselective catalytic oxidation, using tert-butyl hydroperoxide in the presence of chiral titanium complexes. Some mechanistic and stereochemical features of interest were studied in this process. Compound 1 was then subjected to two different substitution reactions with Grignard reagents, which caused two sequentially stereocontrolled carbon-for-carbon displacements, leading to chiral nonracemic dialkyl sulfoxides.

show abstract

Section: Resultsmentioning

confidence: 99%

A Straightforward Enantioselective Route to Dialkyl Sulfoxides Based upon Two Carbon-for-Carbon Substitution Reactions on the Sulfinyl Group

et al. 2002

View full text Add to dashboard Cite

show abstract

“…4. Because the permanganate oxidation of trans ‐cinnamoylcocaine was low yielding, we employed osmium tetroxide as a milder oxidant (13) to produce the diols from cis ‐cinnamoylcocaine. Thus, dihydroxylation of cis ‐cinnamoylcocaine also gave two diastereoisomers in equal amounts ( dr = 50:50), which chromatographed via GC–FID as their di‐TMS derivatives, resulting in peaks #1 and 3 in Fig.…”

Section: Resultsmentioning

confidence: 99%

Four New Illicit Cocaine Impurities from the Oxidation of Crude Cocaine Base: Formation and Characterization of the Diastereomeric 2,3‐Dihydroxy‐3‐Phenylpropionylecgonine Methyl Esters from cis‐ and trans‐Cinnamoylcocaine

Casale

Hays

Toske

et al. 2007

Journal of Forensic Sciences

View full text Add to dashboard Cite

Four new impurities have recently been detected in the gas chromatographic signature profiles of many illicit cocaine hydrochloride exhibits. These impurities are only seen in exhibits that have been oxidized and are most prominent in samples that have been highly oxidized. Exhibits containing these compounds were subjected to gas and liquid chromatographic-mass spectrometric analyses to determine the identity of the impurities. These impurities were subsequently synthesized to verify their structures. Four diastereomeric diols formed from the oxidation of cis- and trans-cinnamoylcocaine were characterized by nuclear magnetic resonance spectrometry, mass spectrometry, and synthesis. Oxidation of cis-cinnamoylcocaine in neutral conditions yielded (2R,3R)-dihydroxy-3-phenylpropionylecgonine methyl ester and (2S,3S)-dihydroxy-3-phenylpropionylecgonine methyl ester, while trans-cinnamoylcocaine produced (2R,3S)-dihydroxy-3-phenylpropionylecgonine methyl ester and (2S,3R)-dihydroxy-3-phenylpropionylecgonine methyl ester. The recent appearance of these new impurities suggests that some illicit cocaine processors have modified their oxidation procedures of crude cocaine base for transformation into illicit refined cocaine hydrochloride.

show abstract

(R,R)‐1,2‐Diphenyl‐1,2‐Ethanediol (Stilbene Diol)

Abstract: (R,R)‐1,2‐diphenyl‐1,2‐ethanediol (stilbene diol) product: (R,R)‐1,2‐diphenyl‐1,2‐ethanediol (stilbene diol)

Cited by 2 publications

References 9 publications

A Straightforward Enantioselective Route to Dialkyl Sulfoxides Based upon Two Carbon-for-Carbon Substitution Reactions on the Sulfinyl Group

A Straightforward Enantioselective Route to Dialkyl Sulfoxides Based upon Two Carbon-for-Carbon Substitution Reactions on the Sulfinyl Group

Four New Illicit Cocaine Impurities from the Oxidation of Crude Cocaine Base: Formation and Characterization of the Diastereomeric 2,3‐Dihydroxy‐3‐Phenylpropionylecgonine Methyl Esters from cis‐ and trans‐Cinnamoylcocaine

Contact Info

Product

Resources

About