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Volumn , Issue 10, 2003, Pages 1904-1914

A new and expedient diastereoselective synthesis of α-(hydroxyamino)phosphonates and α-aminophosphonates by silyl trifiate promoted diethyl phosphite addition to chiral N-benzyl nitrones

Author keywords

Asymmetric synthesis; Enzyme inhibitors; Nitrones; Peptidomimetics; Phosphonates

Indexed keywords

ALDEHYDE DERIVATIVE; NITRONE DERIVATIVE; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORAMIDIC ACID DERIVATIVE; SILANE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

EID: 0038587657     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200200698     Document Type: Article
Times cited : (40)

References (57)
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    • For a short review and some recent articles on the syntheses of α-aminophosphonic acids and α-aminophosphonates, see: Review: [2a] H. Gröger, B. Hammer, Chem. Eur. J. 2000, 6, 943-948. Articles: [2b] R. Kuwano, R. Nishio, Y. Ito, Org. Lett. 1999, 1, 837-839. [2c] B. C. Ranu, A. Hajra, U. Jana, Org. Lett. 1999, 1, 1141-1143. [2d] K. Manabe, S. Kobayashi, Chem. Commun. 2000, 669-670. [2e] I. Schlemninger, Y. Saida, A. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825. [2f] F. Hammerschmidt, M. Hanbauer, J. Org. Chem. 2000, 65, 6121-6131. [2g] G. Castelot-Deliencourt, X. Pannecoucke, J.C. Quirion, Tetrahedron Lett. 2001, 42, 1025-1028. [2h] A. Heydari, M. Zarei, R. Alijanianzadeh, H. Tavakol, Tetrahedron Lett. 2001, 42, 3629-3631. [2i] S. Chandrasekhar, S. Y. Prakash, V. Yagadeshwar, C. Narsihmulu, Tetrahedron Lett. 2001, 42, 5561-5563. [2j] S.-gi Lee, J. H. Park, J. Kang, J. K. Lee, Chem. Commun. 2001, 1698-1699. [2k] I. Schlemminger, A. Willecke, W. Maison, R. Koch, A. Lützen, J. Martens, J. Chem. Soc., Perkin Trans. 1 2001, 2804-2816. [2l] C. Pousset, M. Larchevêque, Tetrahedron Lett. 2002, 43, 5257-5260. [2m] E. Haak, I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2002, 3, 457-463.
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    • Manabe, K.1    Kobayashi, S.2
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    • For a short review and some recent articles on the syntheses of α-aminophosphonic acids and α-aminophosphonates, see: Review: [2a] H. Gröger, B. Hammer, Chem. Eur. J. 2000, 6, 943-948. Articles: [2b] R. Kuwano, R. Nishio, Y. Ito, Org. Lett. 1999, 1, 837-839. [2c] B. C. Ranu, A. Hajra, U. Jana, Org. Lett. 1999, 1, 1141-1143. [2d] K. Manabe, S. Kobayashi, Chem. Commun. 2000, 669-670. [2e] I. Schlemninger, Y. Saida, A. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825. [2f] F. Hammerschmidt, M. Hanbauer, J. Org. Chem. 2000, 65, 6121-6131. [2g] G. Castelot-Deliencourt, X. Pannecoucke, J.C. Quirion, Tetrahedron Lett. 2001, 42, 1025-1028. [2h] A. Heydari, M. Zarei, R. Alijanianzadeh, H. Tavakol, Tetrahedron Lett. 2001, 42, 3629-3631. [2i] S. Chandrasekhar, S. Y. Prakash, V. Yagadeshwar, C. Narsihmulu, Tetrahedron Lett. 2001, 42, 5561-5563. [2j] S.-gi Lee, J. H. Park, J. Kang, J. K. Lee, Chem. Commun. 2001, 1698-1699. [2k] I. Schlemminger, A. Willecke, W. Maison, R. Koch, A. Lützen, J. Martens, J. Chem. Soc., Perkin Trans. 1 2001, 2804-2816. [2l] C. Pousset, M. Larchevêque, Tetrahedron Lett. 2002, 43, 5257-5260. [2m] E. Haak, I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2002, 3, 457-463.
    • (2000) J. Org. Chem. , vol.65 , pp. 4818-4825
    • Schlemninger, I.1    Saida, Y.2    Gröger, A.3    Maison, W.4    Durot, N.5    Sasai, H.6    Shibasaki, M.7    Martens, J.8
  • 7
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    • For a short review and some recent articles on the syntheses of α-aminophosphonic acids and α-aminophosphonates, see: Review: [2a] H. Gröger, B. Hammer, Chem. Eur. J. 2000, 6, 943-948. Articles: [2b] R. Kuwano, R. Nishio, Y. Ito, Org. Lett. 1999, 1, 837-839. [2c] B. C. Ranu, A. Hajra, U. Jana, Org. Lett. 1999, 1, 1141-1143. [2d] K. Manabe, S. Kobayashi, Chem. Commun. 2000, 669-670. [2e] I. Schlemninger, Y. Saida, A. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825. [2f] F. Hammerschmidt, M. Hanbauer, J. Org. Chem. 2000, 65, 6121-6131. [2g] G. Castelot-Deliencourt, X. Pannecoucke, J.C. Quirion, Tetrahedron Lett. 2001, 42, 1025-1028. [2h] A. Heydari, M. Zarei, R. Alijanianzadeh, H. Tavakol, Tetrahedron Lett. 2001, 42, 3629-3631. [2i] S. Chandrasekhar, S. Y. Prakash, V. Yagadeshwar, C. Narsihmulu, Tetrahedron Lett. 2001, 42, 5561-5563. [2j] S.-gi Lee, J. H. Park, J. Kang, J. K. Lee, Chem. Commun. 2001, 1698-1699. [2k] I. Schlemminger, A. Willecke, W. Maison, R. Koch, A. Lützen, J. Martens, J. Chem. Soc., Perkin Trans. 1 2001, 2804-2816. [2l] C. Pousset, M. Larchevêque, Tetrahedron Lett. 2002, 43, 5257-5260. [2m] E. Haak, I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2002, 3, 457-463.
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    • Hammerschmidt, F.1    Hanbauer, M.2
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    • For a short review and some recent articles on the syntheses of α-aminophosphonic acids and α-aminophosphonates, see: Review: [2a] H. Gröger, B. Hammer, Chem. Eur. J. 2000, 6, 943-948. Articles: [2b] R. Kuwano, R. Nishio, Y. Ito, Org. Lett. 1999, 1, 837-839. [2c] B. C. Ranu, A. Hajra, U. Jana, Org. Lett. 1999, 1, 1141-1143. [2d] K. Manabe, S. Kobayashi, Chem. Commun. 2000, 669-670. [2e] I. Schlemninger, Y. Saida, A. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825. [2f] F. Hammerschmidt, M. Hanbauer, J. Org. Chem. 2000, 65, 6121-6131. [2g] G. Castelot-Deliencourt, X. Pannecoucke, J.C. Quirion, Tetrahedron Lett. 2001, 42, 1025-1028. [2h] A. Heydari, M. Zarei, R. Alijanianzadeh, H. Tavakol, Tetrahedron Lett. 2001, 42, 3629-3631. [2i] S. Chandrasekhar, S. Y. Prakash, V. Yagadeshwar, C. Narsihmulu, Tetrahedron Lett. 2001, 42, 5561-5563. [2j] S.-gi Lee, J. H. Park, J. Kang, J. K. Lee, Chem. Commun. 2001, 1698-1699. [2k] I. Schlemminger, A. Willecke, W. Maison, R. Koch, A. Lützen, J. Martens, J. Chem. Soc., Perkin Trans. 1 2001, 2804-2816. [2l] C. Pousset, M. Larchevêque, Tetrahedron Lett. 2002, 43, 5257-5260. [2m] E. Haak, I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2002, 3, 457-463.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1025-1028
    • Castelot-Deliencourt, G.1    Pannecoucke, X.2    Quirion, J.C.3
  • 9
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    • For a short review and some recent articles on the syntheses of α-aminophosphonic acids and α-aminophosphonates, see: Review: [2a] H. Gröger, B. Hammer, Chem. Eur. J. 2000, 6, 943-948. Articles: [2b] R. Kuwano, R. Nishio, Y. Ito, Org. Lett. 1999, 1, 837-839. [2c] B. C. Ranu, A. Hajra, U. Jana, Org. Lett. 1999, 1, 1141-1143. [2d] K. Manabe, S. Kobayashi, Chem. Commun. 2000, 669-670. [2e] I. Schlemninger, Y. Saida, A. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825. [2f] F. Hammerschmidt, M. Hanbauer, J. Org. Chem. 2000, 65, 6121-6131. [2g] G. Castelot-Deliencourt, X. Pannecoucke, J.C. Quirion, Tetrahedron Lett. 2001, 42, 1025-1028. [2h] A. Heydari, M. Zarei, R. Alijanianzadeh, H. Tavakol, Tetrahedron Lett. 2001, 42, 3629-3631. [2i] S. Chandrasekhar, S. Y. Prakash, V. Yagadeshwar, C. Narsihmulu, Tetrahedron Lett. 2001, 42, 5561-5563. [2j] S.-gi Lee, J. H. Park, J. Kang, J. K. Lee, Chem. Commun. 2001, 1698-1699. [2k] I. Schlemminger, A. Willecke, W. Maison, R. Koch, A. Lützen, J. Martens, J. Chem. Soc., Perkin Trans. 1 2001, 2804-2816. [2l] C. Pousset, M. Larchevêque, Tetrahedron Lett. 2002, 43, 5257-5260. [2m] E. Haak, I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2002, 3, 457-463.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 3629-3631
    • Heydari, A.1    Zarei, M.2    Alijanianzadeh, R.3    Tavakol, H.4
  • 10
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    • For a short review and some recent articles on the syntheses of α-aminophosphonic acids and α-aminophosphonates, see: Review: [2a] H. Gröger, B. Hammer, Chem. Eur. J. 2000, 6, 943-948. Articles: [2b] R. Kuwano, R. Nishio, Y. Ito, Org. Lett. 1999, 1, 837-839. [2c] B. C. Ranu, A. Hajra, U. Jana, Org. Lett. 1999, 1, 1141-1143. [2d] K. Manabe, S. Kobayashi, Chem. Commun. 2000, 669-670. [2e] I. Schlemninger, Y. Saida, A. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825. [2f] F. Hammerschmidt, M. Hanbauer, J. Org. Chem. 2000, 65, 6121-6131. [2g] G. Castelot-Deliencourt, X. Pannecoucke, J.C. Quirion, Tetrahedron Lett. 2001, 42, 1025-1028. [2h] A. Heydari, M. Zarei, R. Alijanianzadeh, H. Tavakol, Tetrahedron Lett. 2001, 42, 3629-3631. [2i] S. Chandrasekhar, S. Y. Prakash, V. Yagadeshwar, C. Narsihmulu, Tetrahedron Lett. 2001, 42, 5561-5563. [2j] S.-gi Lee, J. H. Park, J. Kang, J. K. Lee, Chem. Commun. 2001, 1698-1699. [2k] I. Schlemminger, A. Willecke, W. Maison, R. Koch, A. Lützen, J. Martens, J. Chem. Soc., Perkin Trans. 1 2001, 2804-2816. [2l] C. Pousset, M. Larchevêque, Tetrahedron Lett. 2002, 43, 5257-5260. [2m] E. Haak, I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2002, 3, 457-463.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 5561-5563
    • Chandrasekhar, S.1    Prakash, S.Y.2    Yagadeshwar, V.3    Narsihmulu, C.4
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    • For a short review and some recent articles on the syntheses of α-aminophosphonic acids and α-aminophosphonates, see: Review: [2a] H. Gröger, B. Hammer, Chem. Eur. J. 2000, 6, 943-948. Articles: [2b] R. Kuwano, R. Nishio, Y. Ito, Org. Lett. 1999, 1, 837-839. [2c] B. C. Ranu, A. Hajra, U. Jana, Org. Lett. 1999, 1, 1141-1143. [2d] K. Manabe, S. Kobayashi, Chem. Commun. 2000, 669-670. [2e] I. Schlemninger, Y. Saida, A. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825. [2f] F. Hammerschmidt, M. Hanbauer, J. Org. Chem. 2000, 65, 6121-6131. [2g] G. Castelot-Deliencourt, X. Pannecoucke, J.C. Quirion, Tetrahedron Lett. 2001, 42, 1025-1028. [2h] A. Heydari, M. Zarei, R. Alijanianzadeh, H. Tavakol, Tetrahedron Lett. 2001, 42, 3629-3631. [2i] S. Chandrasekhar, S. Y. Prakash, V. Yagadeshwar, C. Narsihmulu, Tetrahedron Lett. 2001, 42, 5561-5563. [2j] S.-gi Lee, J. H. Park, J. Kang, J. K. Lee, Chem. Commun. 2001, 1698-1699. [2k] I. Schlemminger, A. Willecke, W. Maison, R. Koch, A. Lützen, J. Martens, J. Chem. Soc., Perkin Trans. 1 2001, 2804-2816. [2l] C. Pousset, M. Larchevêque, Tetrahedron Lett. 2002, 43, 5257-5260. [2m] E. Haak, I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2002, 3, 457-463.
    • (2001) Chem. Commun. , pp. 1698-1699
    • Lee, S.-Gi.1    Park, J.H.2    Kang, J.3    Lee, J.K.4
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    • For a short review and some recent articles on the syntheses of α-aminophosphonic acids and α-aminophosphonates, see: Review: [2a] H. Gröger, B. Hammer, Chem. Eur. J. 2000, 6, 943-948. Articles: [2b] R. Kuwano, R. Nishio, Y. Ito, Org. Lett. 1999, 1, 837-839. [2c] B. C. Ranu, A. Hajra, U. Jana, Org. Lett. 1999, 1, 1141-1143. [2d] K. Manabe, S. Kobayashi, Chem. Commun. 2000, 669-670. [2e] I. Schlemninger, Y. Saida, A. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825. [2f] F. Hammerschmidt, M. Hanbauer, J. Org. Chem. 2000, 65, 6121-6131. [2g] G. Castelot-Deliencourt, X. Pannecoucke, J.C. Quirion, Tetrahedron Lett. 2001, 42, 1025-1028. [2h] A. Heydari, M. Zarei, R. Alijanianzadeh, H. Tavakol, Tetrahedron Lett. 2001, 42, 3629-3631. [2i] S. Chandrasekhar, S. Y. Prakash, V. Yagadeshwar, C. Narsihmulu, Tetrahedron Lett. 2001, 42, 5561-5563. [2j] S.-gi Lee, J. H. Park, J. Kang, J. K. Lee, Chem. Commun. 2001, 1698-1699. [2k] I. Schlemminger, A. Willecke, W. Maison, R. Koch, A. Lützen, J. Martens, J. Chem. Soc., Perkin Trans. 1 2001, 2804-2816. [2l] C. Pousset, M. Larchevêque, Tetrahedron Lett. 2002, 43, 5257-5260. [2m] E. Haak, I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2002, 3, 457-463.
    • (2001) J. Chem. Soc., Perkin Trans. 1 , pp. 2804-2816
    • Schlemminger, I.1    Willecke, A.2    Maison, W.3    Koch, R.4    Lützen, A.5    Martens, J.6
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    • For a short review and some recent articles on the syntheses of α-aminophosphonic acids and α-aminophosphonates, see: Review: [2a] H. Gröger, B. Hammer, Chem. Eur. J. 2000, 6, 943-948. Articles: [2b] R. Kuwano, R. Nishio, Y. Ito, Org. Lett. 1999, 1, 837-839. [2c] B. C. Ranu, A. Hajra, U. Jana, Org. Lett. 1999, 1, 1141-1143. [2d] K. Manabe, S. Kobayashi, Chem. Commun. 2000, 669-670. [2e] I. Schlemninger, Y. Saida, A. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825. [2f] F. Hammerschmidt, M. Hanbauer, J. Org. Chem. 2000, 65, 6121-6131. [2g] G. Castelot-Deliencourt, X. Pannecoucke, J.C. Quirion, Tetrahedron Lett. 2001, 42, 1025-1028. [2h] A. Heydari, M. Zarei, R. Alijanianzadeh, H. Tavakol, Tetrahedron Lett. 2001, 42, 3629-3631. [2i] S. Chandrasekhar, S. Y. Prakash, V. Yagadeshwar, C. Narsihmulu, Tetrahedron Lett. 2001, 42, 5561-5563. [2j] S.-gi Lee, J. H. Park, J. Kang, J. K. Lee, Chem. Commun. 2001, 1698-1699. [2k] I. Schlemminger, A. Willecke, W. Maison, R. Koch, A. Lützen, J. Martens, J. Chem. Soc., Perkin Trans. 1 2001, 2804-2816. [2l] C. Pousset, M. Larchevêque, Tetrahedron Lett. 2002, 43, 5257-5260. [2m] E. Haak, I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2002, 3, 457-463.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 5257-5260
    • Pousset, C.1    Larchevêque, M.2
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