Cerium(IV) mediated oxygenation of dialkyl malonates: A novel synthesis of tartronic acid derivatives

Tetrahedron Letters

Volumn 39, Issue 18, 1998, Pages 2801-2804

  Nair, Vijay ^a   Nair, Latha G ^a   Mathew, Jessy ^a,b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b Molecumetics Ltd   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; CERIUM; MALONIC ACID DERIVATIVE; TARTRONIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL REACTION; HYDROXYLATION; INFRARED SPECTROSCOPY; MOLECULAR INTERACTION; OXYGENATION; SYNTHESIS;

EID: 0032580513     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00250-0     Document Type: Article

References (18)

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2. (b) Baciochi, E.; Casu, A.; Ruzziconi, R. Tetrahedron. Lett., 1989, 30, 3707.
3. (c) Baciochi, E.; Casu, A.; Ruzziconi, R. Synlett, 1990, 679.
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5. (e) Narasaka, K.; Okauchi, T.; Tanaka, K.; Murakami, M. Chem. Lett. 1992, 2099.
6. 2. (a) Nair , V.; Mathew, J.; Radhakrishnan, K. V. J. Chem. Soc. Perkin Trans. 1, 1996, 1487.
7. (b) Nair , V.; Mathew, J.; Alexander, S Synth. Commun., 1995, 25, 3981.
8. (c) Nair , V.; Mathew, J.; Nair, L.G. Synth. Commun., 1996, 26, 4531.
9. (d) Nair , V.; Mathew, J.; Nair, L.G . Synth. Commun., 1996, 27, 0000.
10. (e) Nair , V.; Mathew, J. J. Chem. Soc. Perkin Tram. I, 1995, 1881.
11. (f) Nair , V.; Mathew, J. J. Chem. Soc. Perkin Trans. I, 1995, 187
12. 3. Nair, V.; Mathew, J.; Prabhakaran J. Chem. Soc. Rev.; 1997, 127 and references sited therein.
13. 4. Except for two isolated reports, there has been no information on the use of CAN in intramolecular reactions. (a). Baciochi, E.; Paolobelli, A. B.; Ruzziconi, R. Tetrahedron, 1992, 48, 4617.
14. (b). Snider, B. B.; Known, T. J. Org. Chem., 1990, 55, 4786.
15. 5. Typical experimental procedure: The ester 1 ( 2.5 mmol) was dissolved in methanol (30 mL) at 0 °C and treated with CAN (5. 75 mmol) in methanol (40 mL). The reaction mixture was gradually brought to room temperature and stirred for 6 h. It was then diluted with water (100 mL) and extracted with dichloromethane(4 × 20 mL). The solvent was evaporated and purified by column chromatography (10% ethyl acetate in hexane as eluent) to afford 2.
16. 5: C , 67 99%; H , 5.37% Found: C , 68.20%; H , 5.48%.
17. 7 Neumann, B.; Muller, S. C.; Hauser, M. J. B.; Steinbock, O.; Simoyi, R. H.; Dalal, N. S. J. Am.Chem. Soc. 1995, 117, 6372.
18. 8. A similar Mn(III) induced reaction of α-allyl β-keto esters with molecular oxygen has been reported: Ohshima, T.;Sodeoka, M.; Shibasaki, M. Tetrahedron. Lett., 1993, 52, 8509.