Synthesis of optically active oxazoles from phosphorylated 2H-azirines and N-protected amino acids or peptides

Tetrahedron Asymmetry

Volumn 13, Issue 23, 2002, Pages 2541-2552

  Palacios, Francisco ^a   Ochoa de Retana, A ^a   Gil, J ^a   Alonso, J ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

(2 AMINOMETHYL 5 METHYL)OXAZOL 4 YLDIPHENYLPHOSPHINE OXIDE; (2 TERT BUTOXYCARBONYLAMINOMETHYL 5 METHYL)OXAZOL 4 YLDIPHENYLPHOSPHINE OXIDE; 5 METHYLOXAZOL 4 YLPHOSPHONATE; [(AMINOETHYL) 5 METHYL]OXAZOL 4 YLDIPHENYLPHOSPHINE OXIDE; [(TERT BUTOXYCARBONYLAMINO 2 PHENYLETHYL) 5 METHYL]OXAZOL 4 YLDIPHENYLPHOSPHINE OXIDE; [(TERT BUTOXYCARBONYLAMINOETHANOYLAMINO) 2 PHENYLETHYL] 5 ETHYLOXAZOL 4 YLPHOSPHONATE; [(TERT BUTOXYCARBONYLAMINOETHANOYLAMINO) 2 PHENYLETHYL] 5 METHYLOXAZOL 4 YLDIPHENYLPHOSPHINE OXIDE; [(TERT BUTOXYCARBONYLAMINOETHYL) 5 METHYL]OXAZOL 4 YLDIPHENYLPHOSPHINE OXIDE; [2 (1 TERT BUTOXYCARBONYLAMINOETHYL) 5 METHYL]OXAZOL 4 YLDIPHENYLPHOSPHINE OXIDE; [2 (1 TERT BUTOXYCARBONYLAMINOETHYL) 5 METHYL]OXAZOL 4 YLPHOSPHONATE; [TERT BUTOXYCARBONYLAMINOETHYL) 5 ETHYL]OXAZOL 4 YLPHOSPHONATE; [TERT BUTOXYCARBONYLAMINOETHYL) 5 METHYL]OXAZOL 4 YLPHOSPHONATE; OXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PHOSPHORYLATION; PRIORITY JOURNAL;

EID: 0037180584     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00686-9     Document Type: Article

References (80)

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52. For recent contributions, see: (a) Koch, K. N.; Linden, A.; Heimgartner, H. Tetrahedron 2001, 57, 2311-2326; (b) Koch, K. N.; Heimgartner, H. Helv. Chim. Acta 2000, 83, 1881-1900; © Koch, K. N.; Linden, A.; Heimgartner, H. Helv. Chim. Acta 2000, 83, 233-257; (d) Lehmann, J.; Linden, A.; Heimgartner, H. Tetrahedron 1999, 55, 5359-5376.
53. For recent contributions, see: (a) Koch, K. N.; Linden, A.; Heimgartner, H. Tetrahedron 2001, 57, 2311-2326; (b) Koch, K. N.; Heimgartner, H. Helv. Chim. Acta 2000, 83, 1881-1900; © Koch, K. N.; Linden, A.; Heimgartner, H. Helv. Chim. Acta 2000, 83, 233-257; (d) Lehmann, J.; Linden, A.; Heimgartner, H. Tetrahedron 1999, 55, 5359-5376.
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65. For recent contributions, see: (a) Cristau, H. J.; Coulombeau, A.; Genevis-Borella, A.; Pirat, J. L. Tetrahedron Lett. 2001, 42, 4491-4494; (b) Georgiadis, D.; Dive, V.; Yiotakis, A. J. Org. Chem. 2001, 66, 6604-6610; © Wallace, E. M.; Moliterni, J. A.; Moskal, M. A.; Neubart, A. D.; Marcopulos, N.; Stamford, L. B.; Trapani, A. J.; Savage, P.; Chou, M.; Jeng, A. Y. J. Med. Chem. 1998, 41, 1513-1523; (d) Meyer, J. H.; Bartlett, P. A. J. Am. Chem. Soc. 1998, 120, 4600-4609; (e) Chen, S.; Coward, J. K. J. Org. Chem. 1998, 63, 502-509; (f) Lohse, P. A.; Felber, R. Tetrahedron Lett. 1998, 39, 2067-2070; (g) Hirschmann, R.; Yager, K. M.; Taylor, C. M.; Witherington, J.; Sprengler, P. A.; Phillips, B. W.; Moore, W.; Smith, A. B. J. Am. Chem. Soc. 1997, 119, 8177-8190.
66. For recent contributions, see: (a) Cristau, H. J.; Coulombeau, A.; Genevis-Borella, A.; Pirat, J. L. Tetrahedron Lett. 2001, 42, 4491-4494; (b) Georgiadis, D.; Dive, V.; Yiotakis, A. J. Org. Chem. 2001, 66, 6604-6610; © Wallace, E. M.; Moliterni, J. A.; Moskal, M. A.; Neubart, A. D.; Marcopulos, N.; Stamford, L. B.; Trapani, A. J.; Savage, P.; Chou, M.; Jeng, A. Y. J. Med. Chem. 1998, 41, 1513-1523; (d) Meyer, J. H.; Bartlett, P. A. J. Am. Chem. Soc. 1998, 120, 4600-4609; (e) Chen, S.; Coward, J. K. J. Org. Chem. 1998, 63, 502-509; (f) Lohse, P. A.; Felber, R. Tetrahedron Lett. 1998, 39, 2067-2070; (g) Hirschmann, R.; Yager, K. M.; Taylor, C. M.; Witherington, J.; Sprengler, P. A.; Phillips, B. W.; Moore, W.; Smith, A. B. J. Am. Chem. Soc. 1997, 119, 8177-8190.
67. For recent contributions, see: (a) Cristau, H. J.; Coulombeau, A.; Genevis-Borella, A.; Pirat, J. L. Tetrahedron Lett. 2001, 42, 4491-4494; (b) Georgiadis, D.; Dive, V.; Yiotakis, A. J. Org. Chem. 2001, 66, 6604-6610; © Wallace, E. M.; Moliterni, J. A.; Moskal, M. A.; Neubart, A. D.; Marcopulos, N.; Stamford, L. B.; Trapani, A. J.; Savage, P.; Chou, M.; Jeng, A. Y. J. Med. Chem. 1998, 41, 1513-1523; (d) Meyer, J. H.; Bartlett, P. A. J. Am. Chem. Soc. 1998, 120, 4600-4609; (e) Chen, S.; Coward, J. K. J. Org. Chem. 1998, 63, 502-509; (f) Lohse, P. A.; Felber, R. Tetrahedron Lett. 1998, 39, 2067-2070; (g) Hirschmann, R.; Yager, K. M.; Taylor, C. M.; Witherington, J.; Sprengler, P. A.; Phillips, B. W.; Moore, W.; Smith, A. B. J. Am. Chem. Soc. 1997, 119, 8177-8190.
68. For recent contributions, see: (a) Cristau, H. J.; Coulombeau, A.; Genevis-Borella, A.; Pirat, J. L. Tetrahedron Lett. 2001, 42, 4491-4494; (b) Georgiadis, D.; Dive, V.; Yiotakis, A. J. Org. Chem. 2001, 66, 6604-6610; © Wallace, E. M.; Moliterni, J. A.; Moskal, M. A.; Neubart, A. D.; Marcopulos, N.; Stamford, L. B.; Trapani, A. J.; Savage, P.; Chou, M.; Jeng, A. Y. J. Med. Chem. 1998, 41, 1513-1523; (d) Meyer, J. H.; Bartlett, P. A. J. Am. Chem. Soc. 1998, 120, 4600-4609; (e) Chen, S.; Coward, J. K. J. Org. Chem. 1998, 63, 502-509; (f) Lohse, P. A.; Felber, R. Tetrahedron Lett. 1998, 39, 2067-2070; (g) Hirschmann, R.; Yager, K. M.; Taylor, C. M.; Witherington, J.; Sprengler, P. A.; Phillips, B. W.; Moore, W.; Smith, A. B. J. Am. Chem. Soc. 1997, 119, 8177-8190.
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70. For recent contributions, see: (a) Cristau, H. J.; Coulombeau, A.; Genevis-Borella, A.; Pirat, J. L. Tetrahedron Lett. 2001, 42, 4491-4494; (b) Georgiadis, D.; Dive, V.; Yiotakis, A. J. Org. Chem. 2001, 66, 6604-6610; © Wallace, E. M.; Moliterni, J. A.; Moskal, M. A.; Neubart, A. D.; Marcopulos, N.; Stamford, L. B.; Trapani, A. J.; Savage, P.; Chou, M.; Jeng, A. Y. J. Med. Chem. 1998, 41, 1513-1523; (d) Meyer, J. H.; Bartlett, P. A. J. Am. Chem. Soc. 1998, 120, 4600-4609; (e) Chen, S.; Coward, J. K. J. Org. Chem. 1998, 63, 502-509; (f) Lohse, P. A.; Felber, R. Tetrahedron Lett. 1998, 39, 2067-2070; (g) Hirschmann, R.; Yager, K. M.; Taylor, C. M.; Witherington, J.; Sprengler, P. A.; Phillips, B. W.; Moore, W.; Smith, A. B. J. Am. Chem. Soc. 1997, 119, 8177-8190.
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