Boronic ester as a linker system for solid phase synthesis

Tetrahedron Letters

Volumn 40, Issue 45, 1999, Pages 7979-7983

  Carboni, Bertrand ^a   Pourbaix, Christelle ^a   Carreaux, François ^a   Deleuze, Hervé ^b   Maillard, Bernard ^b  

^a CNRS   (France)

^b UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE; ARYLBORONIC ACID; BORONIC ACID DERIVATIVE; PHENOL; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ESTERIFICATION; OXIDATION; SOLID;

EID: 0033527699     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01649-4     Document Type: Article

References (31)

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12. The preparation of a polymer-supported 1,3 diol by functionalisation of a chloromethylated resin was first reported by C. C. Leznoff and co-workers: Leznoff, C. C.; Wong, J. Y. Can. J. Chem. 1973, 51, 3756-3764. For more recent references dealing with polymer-supported diol, see: Hodge, P.; Waterhouse, J. J. Chem. Soc., Perkin Trans. 1 1983, 2319-2323. Moberg, C.; Rakos, L. Reactive Polymers 1991, 15, 25-35. Irurre, J.; Fernandez-Serrat, A.; Rosanas, F. Chirality 1997, 9, 191-197. Chandrasekhar, S.; Padmaja, M. B. Synth. Commun. 1998, 28, 3715-3720.
13. The preparation of a polymer-supported 1,3 diol by functionalisation of a chloromethylated resin was first reported by C. C. Leznoff and co-workers: Leznoff, C. C.; Wong, J. Y. Can. J. Chem. 1973, 51, 3756-3764. For more recent references dealing with polymer-supported diol, see: Hodge, P.; Waterhouse, J. J. Chem. Soc., Perkin Trans. 1 1983, 2319-2323. Moberg, C.; Rakos, L. Reactive Polymers 1991, 15, 25-35. Irurre, J.; Fernandez-Serrat, A.; Rosanas, F. Chirality 1997, 9, 191-197. Chandrasekhar, S.; Padmaja, M. B. Synth. Commun. 1998, 28, 3715-3720.
14. The preparation of a polymer-supported 1,3 diol by functionalisation of a chloromethylated resin was first reported by C. C. Leznoff and co-workers: Leznoff, C. C.; Wong, J. Y. Can. J. Chem. 1973, 51, 3756-3764. For more recent references dealing with polymer-supported diol, see: Hodge, P.; Waterhouse, J. J. Chem. Soc., Perkin Trans. 1 1983, 2319-2323. Moberg, C.; Rakos, L. Reactive Polymers 1991, 15, 25-35. Irurre, J.; Fernandez-Serrat, A.; Rosanas, F. Chirality 1997, 9, 191-197. Chandrasekhar, S.; Padmaja, M. B. Synth. Commun. 1998, 28, 3715-3720.
15. The preparation of a polymer-supported 1,3 diol by functionalisation of a chloromethylated resin was first reported by C. C. Leznoff and co-workers: Leznoff, C. C.; Wong, J. Y. Can. J. Chem. 1973, 51, 3756-3764. For more recent references dealing with polymer-supported diol, see: Hodge, P.; Waterhouse, J. J. Chem. Soc., Perkin Trans. 1 1983, 2319-2323. Moberg, C.; Rakos, L. Reactive Polymers 1991, 15, 25-35. Irurre, J.; Fernandez-Serrat, A.; Rosanas, F. Chirality 1997, 9, 191-197. Chandrasekhar, S.; Padmaja, M. B. Synth. Commun. 1998, 28, 3715-3720.
16. The preparation of a polymer-supported 1,3 diol by functionalisation of a chloromethylated resin was first reported by C. C. Leznoff and co-workers: Leznoff, C. C.; Wong, J. Y. Can. J. Chem. 1973, 51, 3756-3764. For more recent references dealing with polymer-supported diol, see: Hodge, P.; Waterhouse, J. J. Chem. Soc., Perkin Trans. 1 1983, 2319-2323. Moberg, C.; Rakos, L. Reactive Polymers 1991, 15, 25-35. Irurre, J.; Fernandez-Serrat, A.; Rosanas, F. Chirality 1997, 9, 191-197. Chandrasekhar, S.; Padmaja, M. B. Synth. Commun. 1998, 28, 3715-3720.
17. We chose to prepare cyclic esters on solid support because of their greater stability compared with the corresponding alkyl alcohol or ethylene glycol derivatives. For the synthesis of boronic esters in solution from the boronic acids, see Ref. 4.
18. 2 adsorption-desorption isotherm is of Class IV with an important hysteresis loop indicating a macroporous structure (Webb, P. A.; Orr, C. Surface area and pore structure by gas adsorption. In Analytical Methods in Fine Particle Technology; Micrometrics Instruments: Norcross, GA, USA, 1997; Chapter 3, p. 53.
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20. 4 and concentrated under reduced pressure to afford the desired pinacol boronate.
21. Methyl boronates are air-sensitive. They were converted to the corresponding stable pinacol esters to allow a more accurate determination of the yield.
22. 1H NMR spectra with those of authentic materials.
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25. For some recent references, see: Hartley, J.; James, T. D. Tetrahedron Lett. 1999, 40, 2597-2600. Eggert, H.; Frederiksen, J.; Morin, C.; Norrild, J. C. J. Org. Chem. 1999, 64, 3846-3852. Ishi-i, T.; Nakashima, K.; Shinkai, S.; Ikeda, A. J. Org. Chem. 1999, 64, 984-990. Gardiner, S. J.; Smith, B. D.; Duggan, P.; Karpa, M. J.; Griffin, G. J. Tetrahedron 1999, 55, 2857-2864 and references therein.
26. For some recent references, see: Hartley, J.; James, T. D. Tetrahedron Lett. 1999, 40, 2597-2600. Eggert, H.; Frederiksen, J.; Morin, C.; Norrild, J. C. J. Org. Chem. 1999, 64, 3846-3852. Ishi-i, T.; Nakashima, K.; Shinkai, S.; Ikeda, A. J. Org. Chem. 1999, 64, 984-990. Gardiner, S. J.; Smith, B. D.; Duggan, P.; Karpa, M. J.; Griffin, G. J. Tetrahedron 1999, 55, 2857-2864 and references therein.
27. For some recent references, see: Hartley, J.; James, T. D. Tetrahedron Lett. 1999, 40, 2597-2600. Eggert, H.; Frederiksen, J.; Morin, C.; Norrild, J. C. J. Org. Chem. 1999, 64, 3846-3852. Ishi-i, T.; Nakashima, K.; Shinkai, S.; Ikeda, A. J. Org. Chem. 1999, 64, 984-990. Gardiner, S. J.; Smith, B. D.; Duggan, P.; Karpa, M. J.; Griffin, G. J. Tetrahedron 1999, 55, 2857-2864 and references therein.
28. For some recent references, see: Hartley, J.; James, T. D. Tetrahedron Lett. 1999, 40, 2597-2600. Eggert, H.; Frederiksen, J.; Morin, C.; Norrild, J. C. J. Org. Chem. 1999, 64, 3846-3852. Ishi-i, T.; Nakashima, K.; Shinkai, S.; Ikeda, A. J. Org. Chem. 1999, 64, 984-990. Gardiner, S. J.; Smith, B. D.; Duggan, P.; Karpa, M. J.; Griffin, G. J. Tetrahedron 1999, 55, 2857-2864 and references therein.
29. Cavallero, C. L.; Herpin, T.; McGuiness, B.; Shimshock, Y. C.; Dolle, R. E. Tetrahedron Lett. 1999, 40, 2711-2714.
30. 4 and concentrated to give the phenol derivative.
31. Brown, H. C.; Snyder, C.; Subba Rao, B. C.; Zweifel, G. Tetrahedron 1986, 42, 5505-5510.