Enantioselective synthesis of an atropisomeric diaryl ether

Angewandte Chemie - International Edition

Volumn 47, Issue 17, 2008, Pages 3234-3237

  Clayden, Jonathan ^a   Worrall, Christopher P ^a   Moran, Wesley J ^a   Helliwell, Madeleine ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Atropisomerism; Conformation analysis; Diaryl ethers; Sulfur

Indexed keywords

CHEMICAL REACTIONS; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

ATROPISOMERISM; CONFORMATION ANALYSIS; DIARYL ETHERS; SULFUR;

ETHERS;

AROMATIC HYDROCARBON; ETHER DERIVATIVE; SULFOXIDE;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; ETHERS; HYDROCARBONS, AROMATIC; MOLECULAR CONFORMATION; STEREOISOMERISM; SULFOXIDES;

EID: 45549091379     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705660     Document Type: Article

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34. In some cases the diastereoisomeric conformers exist as separable atropisomers. For example, 8a showed two spots on TLC; a second elution along a perpendicular axis showed cross-spots indicating interconversion on the plate over a period of minutes. Flash chromatography of 8a allowed us to obtain mixed samples enriched in either diastereoisomer which both equilibrated to the same mixture within 12 hours at room temperature. All ratios reported in Table 1 were measured after ensuring complete equilibration between diastereoisomers.
35. S)-10b) and 669807 ((P)-(-)-17b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre at www.ccdc.cam.ac.uk/data_request/cif.
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