2,2'-Bipyridinium chlorochromate/m-chloroperbenzoic acid-mediated cleavage of cyclic acetals to hydroxyesters

Tetrahedron Letters

Volumn 38, Issue 10, 1997, Pages 1733-1736

  Luzzio, Frederick A ^a   Bobb, Rhiana A ^a  

^a UNIVERSITY OF LOUISVILLE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; BENZOIC ACID DERIVATIVE; CHROMIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; OXIDATION; OXYGENATION; REACTION ANALYSIS;

EID: 0031562432     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00203-7     Document Type: Article

References (16)

1. 1. Presented at the 212th National Meeting of the American Chemical Society, Orlando, Florida, August 28, 1996; ORGN 394.
2. 2. a) Zhang, Z.; Magnusson, G. J. Org. Chem., 1996, 61, 2394-2400.
3. b) Arasappan, A.; Fuchs, P. L. J. Am. Chem. Soc., 1995, 777, 177-183 and references cited therein.
4. For a related transformation see: c) Binkley, R. W.; Goewey, G. S.; Johnston, J. C. J. Org. Chem., 1984, 49, 992-996.
5. d) Sato, K.; Igarashi, T.; Yanagisawa, Y.; Kawauchi, N.; Hashimoto, H.; Yoshimura, J. Chem. Lett., 1988, 1699-1702.
6. 3. a) Chidambaram, N.; Bhat, S.; Chandrasekaran, S. J. Org. Chem., 1992, 57, 5013-5015.
7. For related transformations see: b) Huang, N. J.; Xu, L. Synth. Commun., 1990, 20, 1563-1567.
8. c) Hosokawa, T.; Imada, Y.; Murahashi, S. I. J. Chem. Soc. Chem. Commun., 1983, 1245-1246.
9. d) Delongchamps, P.; Atlani, P.; Frehel, D.; Malaral, A.; Moreau, C. Can. J. Chem., 1974, 3651-3664.
10. e) Prugh, J. D.; McCarthy, W. C. Tetrahedron Lett., 1966, 1351-1356.
11. f) Huyser, E. S.; Garcini, Z. J. Org. Chem., 1962, 27, 2716-2719.
12. 4. Guziec, F. S., Jr.; Luzzio, F. A. Synthesis, 1980, 691-694.
13. 5. Luzzio, F. A.; Guziec, F. S., Jr. Org. Prep. and Proc. Int., 1988, 20, 533-584.
14. 2).
15. 7. Commercially available 2,2′-bipyridinium chlorochromate (Aldrich Chemical Co.) was used for all reactions.
16. 8. This research was assisted financially by a Fulbright-LASPAU Fellowship to RAB. An instrument grant from Glaxo-Wellcome is gratefully acknowledged.