Enantioselective synthesis of α-hydroxyacids through oxidation of terminal alkenes with AD-mix/TEMPO

Tetrahedron Letters

Volumn 41, Issue 17, 2000, Pages 3209-3213

  Javier Aladro, F ^a   Guerra, Francisco M ^a   Javier Moreno Dorado, F ^a   Bustamante, Jesús M ^a   Jorge, Zacarías D ^a   Massanet, Guillermo M ^a  

^a UNIVERSITY OF CÁDIZ   (Spain)

Author keywords

hydroxyacids; Asymmetric dihydroxylation; Oxidation; TEMPO

Indexed keywords

2 HYDROXYACID; ALKENE DERIVATIVE; GLYCOL; SODIUM CHLORATE; SODIUM CHLORITE; TEMPOL;

ARTICLE; ENANTIOMER; HYDROXYLATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0343618760     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00352-X     Document Type: Article

References (27)

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2. For example, for the derivatisation of amines, see: Ho, P. T.; Ngu, K.-Y. J. Org. Chem. 1993, 58, 2313.
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5. MTPA: Methoxy(trifluoromethyl)phenylacetic acid. MPA: Methoxyphenylacetic acid. (a) Dale, J. A.; Dull, D. L.; Mosher H. S. J. Org. Chem. 1969, 34, 2543.
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11. (b) Preparation by oxygenation of chiral imide enolates: Evans, D. A.; Morrissey, M. M.; Dorow, R. L. J. Am. Chem. Soc. 1985, 107, 4346.
12. (c) By asymmetric reduction of α-ketoesters: Brown, H. C.; Cho, B. T.; Park, W. S. J. Org. Chem. 1986, 51, 3398.
13. (d) By stereoselective addition of carbon nucleophiles to chiral α-ketoacids: (i) Akiyama, T.; Ishikawa, K.; Ozaki, S. Synlett 1994, 275; (ii) Kim, Y. H.; Byun, I. S.; Choi, J. Y. Tetrahedron: Asymmetry 1995, 6, 1025; (iii) Basavaiah, D.; Pandiaraju, S.; Bakthadoss, M.; Muthukumaran, K. Tetrahedron: Asymmetry 1996, 7, 997; (iv) Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893.
14. (d) By stereoselective addition of carbon nucleophiles to chiral α-ketoacids: (i) Akiyama, T.; Ishikawa, K.; Ozaki, S. Synlett 1994, 275; (ii) Kim, Y. H.; Byun, I. S.; Choi, J. Y. Tetrahedron: Asymmetry 1995, 6, 1025; (iii) Basavaiah, D.; Pandiaraju, S.; Bakthadoss, M.; Muthukumaran, K. Tetrahedron: Asymmetry 1996, 7, 997; (iv) Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893.
15. (d) By stereoselective addition of carbon nucleophiles to chiral α-ketoacids: (i) Akiyama, T.; Ishikawa, K.; Ozaki, S. Synlett 1994, 275; (ii) Kim, Y. H.; Byun, I. S.; Choi, J. Y. Tetrahedron: Asymmetry 1995, 6, 1025; (iii) Basavaiah, D.; Pandiaraju, S.; Bakthadoss, M.; Muthukumaran, K. Tetrahedron: Asymmetry 1996, 7, 997; (iv) Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893.
16. (d) By stereoselective addition of carbon nucleophiles to chiral α-ketoacids: (i) Akiyama, T.; Ishikawa, K.; Ozaki, S. Synlett 1994, 275; (ii) Kim, Y. H.; Byun, I. S.; Choi, J. Y. Tetrahedron: Asymmetry 1995, 6, 1025; (iii) Basavaiah, D.; Pandiaraju, S.; Bakthadoss, M.; Muthukumaran, K. Tetrahedron: Asymmetry 1996, 7, 997; (iv) Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893.
17. (e) By catalytic enantioselective reduction of trichloromethyl ketones: Corey, E. J.; Link, J. O. Tetrahedron Lett. 1992, 33, 3431.
18. (f) By enzymatic methods: (i) Adam, W.; Fell, R. T.; Hoch, U.; Saha-Möller, C. R.; Schreier, P. Tetrahedron: Asymmetry 1995, 6, 1047; (ii) Adam, W.; Lazarus, M.; Saha-Möller, C. R.; Schreier, P. Tetrahedron: Asymmetry 1996, 7, 2287.
19. (f) By enzymatic methods: (i) Adam, W.; Fell, R. T.; Hoch, U.; Saha-Möller, C. R.; Schreier, P. Tetrahedron: Asymmetry 1995, 6, 1047; (ii) Adam, W.; Lazarus, M.; Saha-Möller, C. R.; Schreier, P. Tetrahedron: Asymmetry 1996, 7, 2287.
20. The Sharpless AD has become so popular that some experiments for undergraduate courses have been developed, for example: Spivey, A. C.; Hanson, R.; Scorah, N.; Thorpe, S. J. J. Chem. Educ. 1999, 76, 655.
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25. The esterification of the resulting α-hydroxyacids proved to be rather difficult. α-Hydroxyacids react to give six-membered lactone dimers. In the case of the benzyl hydroxymethyl malonate, transesterifications may also occur. Ward, R. S. In Bifunctional Compounds; Oxford Chemistry Primers: Oxford, 1994; p. 44.
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27. Other coupling reagents were ineffective. DPTC use: Saitoh, K.; Shiina, I.; Mukaiyama, T. Chem. Lett. 1998, 679.