Efficient, large-scale preparation of (R)- and (S)-1-(2,4,6-triisopropylphenyl)ethanol, versatile chiral auxiliary for cyclopentenone, γ-butyrolactone, and γ-butyrolactam synthesis

Tetrahedron Asymmetry

Volumn 7, Issue 9, 1996, Pages 2707-2710

  Delair, Philippe ^a   Kanazawa, Alice M ^a   De Azevedo, Mariangela B M ^a   Greene, Andrew E ^a  

^a UNIV GRENOBLE ALPES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENONE; GAMMA BUTYROLACTONE; LACTAM DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030248667     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00348-5     Document Type: Article

References (30)

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11. 6. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553. Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926. Cai, D.; Tschaen, D.; Shi, Y.-J.; Verhoeven, T. R.; Reamer, R. A.; Douglas, A. W. Tetrahedron Lett, 1993, 34, 3243-3246. For a review, see: Deloux, L.; Srebnik, M. Chem. Rev. 1993, 95, 763-784.
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21. 6
22. 6
23. 6
24. 14. This procedure is a modification of that described for sec-phenethyl alcohol by Reyes and Juaristi (Reyes, A.; Juaristi, E.; Synth. Commun. 1995, 25, 1053-1058).
25. 15. Fuson, R. C.; Bottorff, E. M.; Speck, S. B. J. Am. Chem. Soc. 1942, 64, 1450-1453.
26. 16. Delair, P.; Kanazawa, A.; Pourashraf, M., unpublished results.
27. 17. Nebois, P.; Greene, A. E. J. Org. Chem., in press.
28. 18. For a description of the experimental techniques and apparatus, see reference 3.
29. 19. a) Merck (R,R)-Whelk-O 1, 5 μm, acetic acid:isopropanol:hexane = 0.5:10:89.5, 1 mL/min.
30. b) Chiracel OD-H, 5 μm, isopropanol:hexane = 2:98, 0.5 mL/min.