Regiospecific hydration of γ-hydroxy-α,β-acetylenic esters: A novel asymmetric synthesis of tetronic acids

Organic Letters

Volumn 8, Issue 10, 2006, Pages 2019-2021

  Rajaram, Amaresh R ^a   Pu, Lin ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALDEHYDE; DRUG DERIVATIVE; ESTER; FURAN DERIVATIVE; TETRONIC ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETYLENE; ALDEHYDES; CATALYSIS; ESTERS; FURANS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33744770021     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060377v     Document Type: Article

References (22)

1. (a) Midland, M. M.; Tramontano, A.; Cable, J. R. J. Org. Chem. 1980, 45, 28-29.
2. (b) Molander, G. A.; St. Jean, D. J., Jr. J. Org. Chem. 2002, 67, 3861-3865.
3. (c) Trost, B. M.; Ball, Z. T. J. Am. Chem. Soc. 2004, 126, 13942-13944.
4. (d) Tejedor, D.; Garcia-Tellado, F.; Marrero-Tellado, J. J.; de Armas, P. Chem. Eur. J. 2003, 9, 3122-3131.
5. (e) Meta, C. T.; Koide, K. Org. Lett. 2004, 6, 1785-1787.
6. (a) Midland, M. M.; McDowell, D. C.; Hatch, R. L.; Tramontano, A. J. Am. Chem. Soc. 1980, 102, 867-869.
7. (b) Noyori, R.; Yamada, T. M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
8. (c) Duvold, T.; Rohmer, M. Tetrahedron Lett. 2000, 41, 3875-3878.
9. (d) Mulzer, J.; Csybowski, M.; Bats, J.-W. Tetrahedron Lett. 2001, 42, 2961-2964.
10. (e) Johansson, M.; B. Köpcke, B.; Anke, H.; Sterner, O. Tetrahedron 2002, 58, 2523-2528.
11. Gao, G.; Wang, Q.; Yu, X.-Q.; Xie, R.-G.; Pu, L. Angew. Chem., Int. Ed. 2005, 45, 122-125.
12. Trost, B. M.; Weiss, A. H.; von Wangelin, A. J. J. Am. Chem. Soc. 2006, 128, 8-9.
13. Hiscox, W.; Jennings, P. W. Organometallics 1990, 9, 1997-1999.
14. Jenning, P. W.; Hartman, J. W.; Hiscox, W. C. Inorg. Chim. Acta 1994, 222, 317-322.
15. (a) Tejedor, D.; Garcia-Tellado, F. Org. Prep. Proced. Int. 2004, 36, 33-59.
16. (b) Roggo, B. E.; Petersen, F.; Delmendo, R.; Jenny, H. B.; Peter, H. H.; Roesel, J. J. Antibiot. 1994, 47, 136-142.
17. (c) Effenberger, F.; Syed, J. Tetrahedron: Asymmetry 1998, 9, 817-825 and references therein.
18. (a) Boll, P. M.; Sorensen, E.; Balieu, E. Acta Chem. Scand. 1968, 22, 3251-3255.
19. (b) Witiak, D. T.; Tehim, A. K. J. Org. Chem. 1990, 55, 1112-1114.
20. (c) Datta, A.; Schmidt, R. R. Synlett 1992, 429-430.
21. (d) Datta, A.; Datta, D.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 8035-8038.
22. (e) Desmaële, D. Tetrahedron 1992, 48, 2925-2934.