Selective oxidation of terminal isopropyl groups to tertiary alcohols by electrochemical methodology

Tetrahedron Letters

Volumn 38, Issue 40, 1997, Pages 7067-7070

  Maki, Shojiro ^a,b   Konno, Katsuhiro ^a   Takayama, Hiroaki ^a  

^a TEIKYO UNIVERSITY   (Japan)

^b UNIVERSITY OF ELECTRO COMMUNICATIONS   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ELECTROLYSIS; IN VITRO STUDY; METHODOLOGY; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030866575     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01650-X     Document Type: Article

References (24)

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3. (a) Bovicelli, P.; Lupattelli, P.; Mincione, E.; Prencipe, T.; Curci, R. J. Org. Chem., 1992, 57, 5052-5054.
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8. (c) For a review, see: Yamamura, S. Electroorganic Synthesis; ed. by Little, R. D. and Weinberg, M. L. Marcel Dekker, Inc.: New York, 1990; pp. 309-315.
9. Similar electrocatalytic oxidation systems were reported: (a) Creager, S. E.; Raybuck, S. A.; Murray, R. W. J. Am. Chem. Soc., 1986, 108, 4225-4227.
10. (b) Balavoine, G.; Barton, D. H. R.; Boivin, J.; Gref, A.; Ozbalik, N.; Riviere, H. Tetrahedron Lett., 1986, 27, 2849-2852.
11. The same results were obtained under a constant potential condition (C. P. E. at -2.4 V vs. SCE; 10 F/mol).
12. 4 as solvent and supporting electrolyte, respectively, were used due to the solubility problem of the substrate.
13. The same oxidation using a metalloporphyrin model system of cytochrome P-450 was reported: Groves. J. T.; Neumann, R. J. J. Org. Chem., 1988, 53, 3892-3893.
14. 3+) of each reaction: Entry 1, 1.3; Entry 2, 1.0; Entry 3, 2.1; Entry 4, 3.5; Entry 5, 8.0; Entry 6, 3.4.
15. (a) Kiegiel, J.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett., 1991, 32, 6057-6060.
16. (b) Trost, B. M.; Dumas, J.; Villa, M. J. Am. Chem. Soc., 1992, 114, 9836-9845.
17. Mascarenas, J. L.; Mourino, A.; Castedo, L. J. Org.Chem., 1986, 51, 1269-1272.
18. 1H NMR spectrum with those of the closely related compounds: Koszewski, N. J.; Reinhardt, T. A.; Beitz, D. C.; Napoli, J. L.; Baggiolini, E. G.; Uskokovic, M. R.; Horst, R. L. Anal. Chem., 1987, 162, 443-452.
19. Jones, G.; Schnoes, H. K.; Levan, L.; DeLuca, H. F. Arch. Biochem. Biophys., 1980, 202, 450-457.
20. No other oxidation product was found in the crude product mixture.
21. 2 due to the difficulty of the purification.
22. 3-hematoporphyrin or hematoporphyrin alone were reversible. This dramatic difference suggested that the interaction of these three reagents plays a key role for the reaction, but the cyclic voltammogram was so complex that the analysis is still underway. We thank Professor Hiroshi Nishihara (The University of Tokyo) for helpful discussion about this subject.
23. The H-type cell (HX-108, Hokuto Denko Co. Ltd.) was used.
24. Bockris, J. O'M.; Devanathan, M. A. V.; Müller, K. Proc. Roy. Soc. London, 1963, A274, 55-79.