Highly efficient chiral resolution and determination of absolute configuration of 2-alkanols by using a cyclopenta[b]furan derivative

Tetrahedron Letters

Volumn 45, Issue 8, 2004, Pages 1667-1670

  Nemoto, Hisao ^a   Tsutsumi, Hiroe ^a   Yuzawa, Satomi ^a   Peng, Xian ^a   Zhong, Weihui ^a   Xie, Jun ^a   Miyoshi, Norikazu ^a   Suzuki, Ichiro ^a   Shibuya, Masayuki ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Acetal; Alkenyl ether; Chiral resolution; Thin layer chromatography

Indexed keywords

3A BENZHYDRYL 3,3A,4,5 TETRAHYDRO 2H CYCLOPENTA[B]FURAN; ALKANOL; BENZHYDRYL DERIVATIVE; FURAN DERIVATIVE; METHANE; PYRIDINIUM DERIVATIVE; SILICA GEL; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; GEL CHROMATOGRAPHY;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0842305159     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.104     Document Type: Article

References (20)

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15. 254).
16. f values for 14c and 15c , we used the hexane/toluene eluent system for all subsequent TLC procedures.
17. f value of the diastereomers produced from (±)-8 and various (±)-2-alkanols. Then, we prepared optically active 14 and 15 by the reaction of either (±)-8 and optically active 2-alkanols, or optically active 8 and DL-2-alkanols. Accordingly, all the relative and absolute configurations of 14 and 15 were determined.
18. A typical example of publication describing the determination of absolute configuration using the formation of diastereomers: Ohtani I., Kusumi T., Kashman Y., Kakisawa H. J. Am. Chem. Soc. 113:1991;4092-4096.
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20. f value could be produced by the skeleton of hexahydrocyclopenta[b] furan.