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Volumn 14, Issue 6, 2003, Pages 689-700

Asymmetric synthesis of 2H-aziridine phosphonates, and α- or β-aminophosphonates from enantiomerically enriched 2H-azirines

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKALOID DERIVATIVE; AMINE; AZIRIDINE DERIVATIVE; DIETHYL[1 (4 TOLUENESULFONYLAMINO)BUTYL]PHOSPHONATE; DIETHYL[2 (4 TOLUENESULFONYLAMINO)BUTYL]PHOSPHONATE; DIETHYL[2 (4 TOLUENESULFONYLAMINO)PROPYL]PHOSPHONATE; DIETHYL[2 PHENYL 1 (4 TOLUENESULFONYLAMINO)ETHYL]PHOSPHONATE; OXIME DERIVATIVE; PHOSPHORAMIDIC ACID; SODIUM BOROHYDRIDE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

EID: 0037459247     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00089-2     Document Type: Article
Times cited : (84)

References (99)
  • 1
    • 0036340599 scopus 로고    scopus 로고
    • For recent reviews on azirines, see: (a) Palacios, F.; Ochoa de Retana, A. M.; Martínez de Marigorta, E.; de los Santos, J. M. Org. Prep. Proced. Int. 2002, 34, 219-269; (b) Gilchrist, T. L. Aldrichim. Acta 2001, 34, 51-55; © Zwanenburg, B.; ten Holte, P. Top. Cur. Chem. 2001, 216, 93-124; (d) Palacios, F.; Ochoa de Retana, A. M.; Martínez de Marigorta, E.; de los Santos, J. M. Eur. J. Org. Chem. 2001, 2401-2414.
    • (2002) Org. Prep. Proced. Int. , vol.34 , pp. 219-269
    • Palacios, F.1    Ochoa De Retana, A.M.2    Martínez De Marigorta, E.3    De Los Santos, M.4
  • 2
    • 0003007605 scopus 로고    scopus 로고
    • For recent reviews on azirines, see: (a) Palacios, F.; Ochoa de Retana, A. M.; Martínez de Marigorta, E.; de los Santos, J. M. Org. Prep. Proced. Int. 2002, 34, 219-269; (b) Gilchrist, T. L. Aldrichim. Acta 2001, 34, 51-55; © Zwanenburg, B.; ten Holte, P. Top. Cur. Chem. 2001, 216, 93-124; (d) Palacios, F.; Ochoa de Retana, A. M.; Martínez de Marigorta, E.; de los Santos, J. M. Eur. J. Org. Chem. 2001, 2401-2414.
    • (2001) Aldrichim. Acta , vol.34 , pp. 51-55
    • Gilchrist, T.L.1
  • 3
    • 0036340599 scopus 로고    scopus 로고
    • For recent reviews on azirines, see: (a) Palacios, F.; Ochoa de Retana, A. M.; Martínez de Marigorta, E.; de los Santos, J. M. Org. Prep. Proced. Int. 2002, 34, 219-269; (b) Gilchrist, T. L. Aldrichim. Acta 2001, 34, 51-55; © Zwanenburg, B.; ten Holte, P. Top. Cur. Chem. 2001, 216, 93-124; (d) Palacios, F.; Ochoa de Retana, A. M.; Martínez de Marigorta, E.; de los Santos, J. M. Eur. J. Org. Chem. 2001, 2401-2414.
    • (2001) Top. Cur. Chem. , vol.216 , pp. 93-124
    • Zwanenburg, B.1    Ten Holte, P.2
  • 4
    • 0034950899 scopus 로고    scopus 로고
    • For recent reviews on azirines, see: (a) Palacios, F.; Ochoa de Retana, A. M.; Martínez de Marigorta, E.; de los Santos, J. M. Org. Prep. Proced. Int. 2002, 34, 219-269; (b) Gilchrist, T. L. Aldrichim. Acta 2001, 34, 51-55; © Zwanenburg, B.; ten Holte, P. Top. Cur. Chem. 2001, 216, 93-124; (d) Palacios, F.; Ochoa de Retana, A. M.; Martínez de Marigorta, E.; de los Santos, J. M. Eur. J. Org. Chem. 2001, 2401-2414.
    • (2001) Eur. J. Org. Chem. , pp. 2401-2414
    • Palacios, F.1    Ochoa De Retana, A.M.2    Martínez De Marigorta, E.3    De Los Santos, J.M.4
  • 23
    • 0034879581 scopus 로고    scopus 로고
    • For recent contributions, see: (a) Smoukov, S. K.; Telser, J.; Bernat, B. A.; Rife, C. L.; Armstrong, R. N.; Hoffman, B. M. J. Am. Chem. Soc. 2002, 124, 2318-2326; (b) Samland, A. K.; Jelesarov, I.; Kuhn, R.; Amrhein, N.; Macheroux, P. Biochem. 2001, 40, 9950-9956; © Schulin, T. J. Ant. Chemother. 2002, 49, 403-406; (d) Grif, K.; Dierich, M. P.; Pfaller, K.; Miglioli, P. A.; Allenberger, F. J. Ant. Chemother. 2001, 48, 209-217; (e) Gray, K. J.; Gascoyne-Binzi, D. M.; Nicholsn, P.; Heritage, J.; Hawkey, P. M. J. Ant. Chemother. 2001, 48, 744-745
    • For recent contributions, see: (a) Smoukov, S. K.; Telser, J.; Bernat, B. A.; Rife, C. L.; Armstrong, R. N.; Hoffman, B. M. J. Am. Chem. Soc. 2002, 124, 2318-2326; (b) Samland, A. K.; Jelesarov, I.; Kuhn, R.; Amrhein, N.; Macheroux, P. Biochem. 2001, 40, 9950-9956; © Schulin, T. J. Ant. Chemother. 2002, 49, 403-406; (d) Grif, K.; Dierich, M. P.; Pfaller, K.; Miglioli, P. A.; Allenberger, F. J. Ant. Chemother. 2001, 48, 209-217; (e) Gray, K. J.; Gascoyne-Binzi, D. M.; Nicholsn, P.; Heritage, J.; Hawkey, P. M. J. Ant. Chemother. 2001, 48, 744-745.
  • 24
    • 84992585492 scopus 로고    scopus 로고
    • For reviews, see: (a) Engel, R. In Handbook of Organophosphorus Chemistry, M. Dekker, Inc.: New York, 1992; (b) Kafarski, P.; Lejezak, B. Phosphorus & Sulfur 1991, 63, 193-215; © Hoagland, R. E. In Biologically Active Natural Products, Culter, H. G., Ed.; ACS Symposium Series 380. American Chemical Society, Washington DC, 1988, p. 182; (d) Toy, A. D. F.; Walsh, E. N. In Phosphorus Chemistry in Everyday Living, American Chemical Society, Washington DC, 1987, p. 333
    • For reviews, see: (a) Engel, R. In Handbook of Organophosphorus Chemistry, M. Dekker, Inc.: New York, 1992; (b) Kafarski, P.; Lejezak, B. Phosphorus & Sulfur 1991, 63, 193-215; © Hoagland, R. E. In Biologically Active Natural Products, Culter, H. G., Ed.; ACS Symposium Series 380. American Chemical Society, Washington DC, 1988, p. 182; (d) Toy, A. D. F.; Walsh, E. N. In Phosphorus Chemistry in Everyday Living, American Chemical Society, Washington DC, 1987, p. 333.
  • 32
    • 84992636860 scopus 로고    scopus 로고
    • For reviews, see: (a) Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity. In Kukhar, V. P.; Hudson, H. R., Eds.; Wiley: Chichester, 2000; (b) Fields, S. F. Tetrahedron 1999, 55, 12237-12273; © Hiratake, J.; Oda, J. Biosci. Biotech. Biochem. 1997, 61, 211-218
    • For reviews, see: (a) Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity. In Kukhar, V. P.; Hudson, H. R., Eds.; Wiley: Chichester, 2000; (b) Fields, S. F. Tetrahedron 1999, 55, 12237-12273; © Hiratake, J.; Oda, J. Biosci. Biotech. Biochem. 1997, 61, 211-218.
  • 54
    • 84963388098 scopus 로고
    • Maier L., Diel P.J. Phosphorus Sulfur Silicon. 90:1994;259-279 Gonella, J.; Reiner, A. Eur. Pat. Appl. EP. 693, 494, 1996 [Chem. Abstr. 1996, 124, 261358k] Johnson, R. A. US US 5, 347, 029, 1994 [Chem. Abstr. 1995, 122, 31708d].
    • (1994) Phosphorus Sulfur Silicon , vol.90 , pp. 259-279
    • Maier, L.1    Diel, P.J.2
  • 84
    • 84992641362 scopus 로고    scopus 로고
    • The enantiopurity of enantiomerically enriched 2H-azirines 6 was determined by HPLC analysis using a Daicel Chiralpak AD-H (4.6×250 mm) chiral column at 25°C using MS detection by chemical ionization (CI)
    • The enantiopurity of enantiomerically enriched 2H-azirines 6 was determined by HPLC analysis using a Daicel Chiralpak AD-H (4.6×250 mm) chiral column at 25°C using MS detection by chemical ionization (CI).
  • 85
    • 84992638261 scopus 로고    scopus 로고
    • 25 was found, whereas a linear relationship was detected when excess of quinine was used
    • 25 was found, whereas a linear relationship was detected when excess of quinine was used.
  • 87
    • 0035513451 scopus 로고    scopus 로고
    • For recent contributions on polymer-bound amine reactions, see: (a) Morgan, T.; Ray, N. C.; Parry, D. M. Org. Lett. 2002, 4, 597-598; (b) Kilbrun, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron 2002, 58, 1739-1743; © Zheng, C.; Combs, A. P. J. Comb. Chem. 2002, 4, 38-43; (d) Larsen, S. D.; Dipaolo, B. A. Org. Lett. 2001, 3, 3341-3344; (e) Dener, J. M.; Lease, T. G.; Novack, A. R.; Plunkett, M. J.; Hocker, M. D.; Fantauzzi, P. P. J. Comb. Chem. 2001, 3, 590-597
    • For recent contributions on polymer-bound amine reactions, see: (a) Morgan, T.; Ray, N. C.; Parry, D. M. Org. Lett. 2002, 4, 597-598; (b) Kilbrun, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron 2002, 58, 1739-1743; © Zheng, C.; Combs, A. P. J. Comb. Chem. 2002, 4, 38-43; (d) Larsen, S. D.; Dipaolo, B. A. Org. Lett. 2001, 3, 3341-3344; (e) Dener, J. M.; Lease, T. G.; Novack, A. R.; Plunkett, M. J.; Hocker, M. D.; Fantauzzi, P. P. J. Comb. Chem. 2001, 3, 590-597.
  • 88
    • 84992641381 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Nicolaou, K. C.; Pfefferkorn, J. A. Biopolymers 2001, 60, 171-193; (b) Kauhaluoma, Y. Tetrahedron 2001, 57, 7053-7071; © Nefti, A.; Ostresh, J. M.; Houghten, R. A. In Solid-Phase Synthesis, Kates, S. A.; Albericio, F., Eds.; Marcel Dekker: New York, 2000; pp. 617-647; (d) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091-2157; (e) Franzen, F. R. G. J. Comb. Chem. 2000, 2, 195-214
    • For recent reviews, see: (a) Nicolaou, K. C.; Pfefferkorn, J. A. Biopolymers 2001, 60, 171-193; (b) Kauhaluoma, Y. Tetrahedron 2001, 57, 7053-7071; © Nefti, A.; Ostresh, J. M.; Houghten, R. A. In Solid-Phase Synthesis, Kates, S. A.; Albericio, F., Eds.; Marcel Dekker: New York, 2000; pp. 617-647; (d) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091-2157; (e) Franzen, F. R. G. J. Comb. Chem. 2000, 2, 195-214.
  • 89
    • 84992641393 scopus 로고    scopus 로고
    • For recent contributions, see: (a) Cheng, W. C.; Wong, M.; Olmstead, M. M.; Kurth, M. J. Org. Lett. 2002, 4, 741-744; (b) Nefti, A.; Ostresh, J. M.; Houghten, R. A. Biopolymers 2001, 60, 212-219; © Caba, J. M.; Rodríguez, I. M.; Manzanares, I.; Giralt, E.; Albericio, F. J. Org. Chem. 2001, 66, 7568-7574; (d) Larsen, S. D.; Dipaolo, B. A. Org. Lett. 2001, 3, 3341-3344; (e) Gopalsamy, A.; Yang, H. J. Comb. Chem. 2001, 3, 278-283
    • For recent contributions, see: (a) Cheng, W. C.; Wong, M.; Olmstead, M. M.; Kurth, M. J. Org. Lett. 2002, 4, 741-744; (b) Nefti, A.; Ostresh, J. M.; Houghten, R. A. Biopolymers 2001, 60, 212-219; © Caba, J. M.; Rodríguez, I. M.; Manzanares, I.; Giralt, E.; Albericio, F. J. Org. Chem. 2001, 66, 7568-7574; (d) Larsen, S. D.; Dipaolo, B. A. Org. Lett. 2001, 3, 3341-3344; (e) Gopalsamy, A.; Yang, H. J. Comb. Chem. 2001, 3, 278-283.
  • 96
    • 84992594337 scopus 로고    scopus 로고
    • 34
    • 34.


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