Enantioselective rearrangements of bicyclo[2.2.1]- and bicyclo[2.2.2]alkene-derived achiral epoxides to ketones

Tetrahedron Asymmetry

Volumn 8, Issue 4, 1997, Pages 519-521

  Hodgson, David M ^a   Marriott, Robert E ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; KETONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031579452     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00014-1     Document Type: Article

References (10)

1. 1. Crandall, J. K.; Apparu, M. Org. React. (N. Y.) 1983, 29, 345-443; Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
2. 1. Crandall, J. K.; Apparu, M. Org. React. (N. Y.) 1983, 29, 345-443; Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
3. 2. Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384.
4. 3. Hodgson, D. M.; Wisedale, R. Tetrahedron: Asymmetry 1996, 7, 1275-1276.
5. 2O, reflux): Crandall, J. K.; Crawley, L. C.; Banks, D. B.; Lin, L. C. J. Org. Chem. 1971, 36, 510-513, see also ref. 1 above.
6. 5. Yanagisawa, A.; Yasue, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1994, 2103-2104.
7. 6. Isolated total yields of chromatographically homogeneous, spectroscopically pure products are reported. Ees were determined as follows: ketone 8 and norcamphor 12 by HPLC (Daicel Chiralpak AD column, EtOH and 30:70 EtOH/hexane as eluents respectively) after reduction (L-Selectride®) and 3,5-dinitrobenzoate derivatisation of the resulting endo-alcohols; nortricyclanol 3 and alcohol 17 by HPLC (5:95 EtOH/hexane and 25:75 EtOH/hexane as eluents respectively) of the corresponding 3,5-dinitrobenzoates. Op of ketone 16 by comparison of magnitude of [α]D with lit. {[α]D -520 for >98% ee material: Demuth, M.; Chandrasekhar, S.; Schaffner, K. J. Am. Chem. Soc. 1984, 106, 1092-1095}.
8. 7. Reactions of epoxides 9 and 13 with LDA: Hodgson, D. M.; Marriott, R. E. Tetrahedron Lett. 1997, 38, 887-888.
9. 8. Correlation of sign of specific rotation of norcamphor 12 with absolute configuration: Berson, J. A.; Walia, J. S.; Remanick, A.; Suzuki, S.; Reynolds-Warnhoff, P.; Willner, D. J. Am. Chem. Soc. 1961, 83, 3986-3997.
10. 9. Bambridge, K.; Begley, M. J.; Simpkins, N. S. Tetrahedron Lett. 1994, 35, 3391-3394.