Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1577-1580

  Dalla, Vincent ^a   Cotelle, Philippe ^a   Catteau, Jean Pierre ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; KETONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; REDUCTION;

EID: 0031550852     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00154-8     Document Type: Article

References (23)

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4. 3 Guerrier, L.; Royer, J.; Grierson, D.; Husson, H. P. J. Am. Chem. Soc. 1983, 105, 7754-7755. Marco, J. L.; Royer, J.; Husson, H. P. Synth. Com. 1987, 17, 669-676.
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16. 3) δ 7.46 (1H, d, J=1.7 Hz), 7.24 (1H, dd, J=8.4 Hz, J=1.7 Hz), 6.85 (1H, d, J=8.4 Hz), 6.48 (1H, ethylenic, s), 6.35 (1H, br, s, OH), 3.88 (9H, 3s)
17. 11. For such an acidic catalysis already used in the reduction of α-amino acids, see: Abiko, A.; Masamune, S. Tetrahedron. Lett. 1992, 33, 5517-5518.
18. 12. Stockmayer, W. H.; Rice, D. W.; Stephenson, C. C. J. Am. Chem. Soc. 1955, 77, 1980-1983.
19. 13. For a ref. dealing with the influence of the nature of the solvent on the mode of reduction of hydrides, see : Krishnamurthy, S. J. Org. Chem. 1980, 45, 2550-2551.
20. 2 was very smooth in comparison with the case of methanol
21. 15. For a similar effect of a nitro substituent on the reduction's rate of hydride, see : Pelter, A.; Smith, K. In Comprehensive Organic Chemistry, Barton, D. and Ollis, W. D. Ed., 1979, 3, p767.
22. 17 gave satisfactory yields of esters. Finally, carrying out the AcCl-mediated esterification upon heating was the best compromise and esters 4a-e were obtained up to 70%. Note that these isolated methyl esters, and particularly 4a-b were also subject to a rapid decomposition into benzaldehydes when stored at room temperature, and had to be used freshly after being prepared. On the other hand, nitro esters 4f-g were stable several weeks at r.t.
23. 17. Namiki, T.; Suzuki, Y.; Sawada, K.; Itoh, Y.; Oka, T.; Kitaura, Y.; Hashimoto, M. Chem. Pharm. Bull. 1987, 2594-2597.