Sml2-Promoted Oxidation of Aldehydes in the Presence of Electron-Rich Heteroatoms

Organic Letters

Volumn 4, Issue 25, 2002, Pages 4539-4541

  Smith III, Amos B ^a   Lee, Dongjoo ^a   Adams, Christopher M ^a   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ESTER; KETONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; OXIDATION REDUCTION REACTION;

ALDEHYDES; ELECTRONS; ESTERS; KETONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 0037069712     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027095p     Document Type: Article

References (29)

1. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7.
2. (a) Smith, A. B., III; Guaciaro, M. A.; Schow, S. R.; Wovkulich, P. M.; Toder, B. H.; Hall, T. W. J. Am. Chem. Soc. 1981, 103, 219.
3. (b) Smith, A. B., III; Dorsey, B. D.; Visnick, M.; Maeda, T.; Malamas, M. S. J. Am. Chem. Soc. 1986, 108, 3110.
4. (c) Smith, A. B., III; Chen, K.; Robinson, D. J.; Laasko, L. M.; Hale, K. J. Tetrahedron Lett. 1994, 35, 4271.
5. (d) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011.
6. (e) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. J., Jr. J. Am. Chem. Soc. 1997, 119, 962.
7. (f) Smith, A. B., III; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925.
8. (g) Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 37, 35-46.
9. (h) Smith, A. B., III; Friestad, G. K.; Barbosa, J.; Bertounesque, E.; Hull, K. G.; Iwashima, M.; Qiu, Y.; Salvatore, B. A.; Spoors, P. G.; Duan, J. J.-W. J. Am. Chem. Soc. 1999, 121, 10468.
10. (i) Smith, A. B., III; Lin, Q. Y.; Doughty, V. A.; Zhuang, L.; McBriar, M. D.; Kerns, J. K.; Brook, C. S.; Murase, N.; Nakayama, K. Angew. Chem., Int. Ed. 2001, 40, 196.
11. (j) Smith, A. B.; Doughty, V. A.; Sfouggatakis, C.; Bennett, C. S.; Koyanagi, J.; Takeuchi, M. Org. Lett. 2002, 4, 783.
12. (k) Smith, A. B., III; Pitram, S. M. Org. Lett. 1999, 1, 2001.
13. (l) Smith, A. B., III; Pitram, S. M.; Gaunt, M. J.; Kozmin, S. A. J. Am. Chem. Soc. In press.
14. Smith, A. B., III; Adams, C. A.; Barbosa, S. A. L.; Degnan, A. P. J. Am. Chem. Soc. Submitted for publication.
15. Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447.
16. Konosu, T.; Oida, S. Chem. Pharm. Bull. 1993, 41, 1012.
17. 3/MeOH) with those of both known anti-1,3 diol and syn-1,3 diol.
18. Experimental procedures for the synthesis of all new compounds can be found in Supporting Information.
19. Parikh, J. R.; von Doering, W. E. J. Am. Chem. Soc. 1967, 89, 5505.
20. (a) Kunz, H.; Waldmann, H. Helv. Chim. Acta 1985, 68, 618.
21. (b) Kunz, H.; Waldmann, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 71.
22. (c) Jeffrey, P. D.; McCombie, S. W. J. Org. Chem. 1982, 47, 587-590.
23. (a) Nakamura, H.; Arata, K.; Wakamatsu, T.; Ban, Y.; Shibasaki, M. Chem. Pharm. Bull. 1990, 38, 2435.
24. (b) Node, M.; Hori, H.; Fujita, E. J. Chem. Soc., Perkin Trans. 1 1976, 2237.
25. Attempts at Pd-mediated hydrogenolysis proved to be unsuccessful, presumably due to sulfur poisoning of the catalyst.
26. Yoo, S.-E.; Kim, H. R.; Yi, K. Y. Tetrahedron Lett. 1990, 31, 5913.
27. Schmitz, F. J.; Gunasekera, S. P.; Yalamanchili, G.; Hossain, M. B.; van der Helm, D. J. Am. Chem. Soc. 1984, 106, 7251.
28. Smith, A. B., III; Lodise, S. A. Org. Lett. 1999, 1, 1249.
29. Fusetani, N.; Sugawara, T.; Matsunaga, S.; Hirota, H. J. Org. Chem. 1991, 56, 4971.