Facile cleavage of vicinal tertiary diols by pyridinium dichromate

Journal of the Indian Chemical Society

Volumn 77, Issue 11-12, 2000, Pages 651-655

  Maki, Shojiro ^a   Ishihara, Jun ^a   Nakanishi, Koji ^a  

^a Columbia University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMIC ACID; HYDROXYL GROUP; KETONE DERIVATIVE; PYRIDINIUM DERIVATIVE; PYRIDINIUM DICHROMATE; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; CONFERENCE PAPER; OXIDATION; SPECTROMETRY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034437041     PISSN: 00194522     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Conference Paper

References (10)

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3. (a) R. Criegee, Chem. Ber., 1931, 64, 260;
4. (b) B. Achmatowicz, and J. Wicha, Tetrahedron Lett., 1987, 28, 2999.
5. G. Ohloff and W. Giersch, Angew. Chem., 1973, 85, 401.
6. A. McKillop and R. A. Raphael, J. Org. Chem., 1972, 37, 4204.
7. B. Jaselskis and S. Vas, J. Am. Chem. Soc., 1964, 86, 2078.
8. A. J. Cisneros, S. Fernandez and J. E. Hernandez, Synth. Commun., 1982, 12, 833.
9. I. Ohtani, T. Kusumi, Y. Kashman and H. Kakisawa, J. Am. Chem. Soc., 1991, 113, 4092. On the basis of 11, configurations of compound 5-10 and 12 were determined.
10. The (S)- and (R)-MTPA esters 12 were prepared in quantitative yield by reaction of diketo carbinol 11 with MTPA chloride and DMAP in methylene chloride, rt, 4 h, (Chemical Equation Presented)