Cyclopentanes from N-aminoglyconolactams: Reaction mechanism and improved access to diazocyclopentanones

Helvetica Chimica Acta

Volumn 87, Issue 9, 2004, Pages 2434-2446

  Hu, Guixian ^a   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DECOMPOSITION; KETONES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CYCLOPENTANES; EPIMERS;

AMINO ACIDS;

4 O [(TERT BUTYL)DIMETHYLSILYL] 5 DEOXY 5 HYDRAZONO 2,3 O ISOPROPYLIDENE RIBONO 1,5 LACTAM; 4 TOLUENESULFONOHYDRAZIDE; 5 AMINO 4 O [(TERT BUTYL)DIMETHYLSILYL] 5 DEOXY 2,3 O ISOPROPYLIDENE [[(4 METHYLPHENYL)SULFONYL]AMINO]RIBONO 1,5 LACTAM; 5 C ACETOXY 4 O [(TERT BUTYL)DIMETHYLSILYL] 2,3 O ISOPROPYLIDENE RIBONO 1,5 LACTONE; 5 O ACETYL 1,5 RIBONOLACTONE; 5 O ACETYL 5 AMINO 4 O [(TERT BUTYL)DIMETHYLSILYL] 2,3 O ISOPROPYLIDENE N [[(4 METHYLPHENYL)SULFONYL]AMINO]RIBONO 1,5 LACTAM; ACETOHYDRAZIDE; ACETOXY DIAZEPINONE; CARBENE; CYCLOPENTANE; CYCLOPENTANONE DERIVATIVE; DIAZEPINE DERIVATIVE; DIAZOCYCLOPENTANONE; HYDRAZIDE DERIVATIVE; LACTAM DERIVATIVE; LACTONE DERIVATIVE; N ACETAMIDO 5 AMINO 4 O [(TERT BUTYL)DIMETHYLSILYL] 5 DEOXY 2,3 BIS O (METHOXYMETHYL)ARABINONO 1,5 LACTAM; N ACETAMIDO 5 AMINO 4 O [(TERT BUTYL)DIMETHYLSILYL] 5 DEOXY 2,3 BIS O (METHOXYMETHYL)XYLONO 1,5 LACTAM; N ACETAMIDO 5 AMINO 4 O [(TERT BUTYL)DIMETHYLSILYL] 5 DEOXY 2,3 O ISOPROPYLIDENE LYXONO 1,3 LACTAM; N ACETAMIDO 5 AMINO 4 O [(TERT BUTYL)DIMETHYLSILYL] 5 DEOXY 2,3 O ISOPROPYLIDENE RIBONO 1,5 LACTAM; N ACETAMIDO 5 O ACETYL 5 AMINO 4 O [(TERT BUTYL)DIMETHYLSILYL] 2,3 O ISOPROPYLIDENE RIBONO 1,5 LACTAM; N ACETAMIDOLYXONOLACTAM; N AMINOGLYCONOLACTAM; OXADIAZOLINE; RIBONOLACTONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; EPIMER; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 5644230883     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200490218     Document Type: Article

References (20)

1. G. Hu, A. Vasella, Helv. Chim. Acta 2004, 87, 2405.
2. J. P. Freeman, J. Org. Chem. 1964, 29, 1379.
3. D. C. Iffland, L. Salisbury, W. R. Schafer, J. Am. Chem. Soc. 1961, 83, 747; R. W. Hoffmann, H. J. Luthardt, Tetrahedron Lett. 1966, 7, 411.
4. D. C. Iffland, L. Salisbury, W. R. Schafer, J. Am. Chem. Soc. 1961, 83, 747; R. W. Hoffmann, H. J. Luthardt, Tetrahedron Lett. 1966, 7, 411.
5. T. E. Walker, H. P. C. Hogenkamp, Carbohydr. Res. 1974, 32, 413.
6. I. Maeba, M. Suzuki, O. Hara, T. Takeuchi, T. Iijima, H. Furukawa, J. Org. Chem. 1987, 52, 4521; F. Delgado, M. M. Martín, M. V. Martín, Tetrahedron 2001, 57, 4389; A. Dinsmore, P. M. Doyle, M. Steger, D. W. Young, J. Chem. Soc., Perkin Trans 1 2002, 613.
7. I. Maeba, M. Suzuki, O. Hara, T. Takeuchi, T. Iijima, H. Furukawa, J. Org. Chem. 1987, 52, 4521; F. Delgado, M. M. Martín, M. V. Martín, Tetrahedron 2001, 57, 4389; A. Dinsmore, P. M. Doyle, M. Steger, D. W. Young, J. Chem. Soc., Perkin Trans 1 2002, 613.
8. I. Maeba, M. Suzuki, O. Hara, T. Takeuchi, T. Iijima, H. Furukawa, J. Org. Chem. 1987, 52, 4521; F. Delgado, M. M. Martín, M. V. Martín, Tetrahedron 2001, 57, 4389; A. Dinsmore, P. M. Doyle, M. Steger, D. W. Young, J. Chem. Soc., Perkin Trans 1 2002, 613.
9. R. N. Butler, F. L. Scott, T. A. F. O'Mahony, Chem. Rev. 1973, 73, 93; R. N. Butler, Chem. Rev. 1984, 84, 249; A. Kotali, Curr. Org. Chem. 2002, 6, 965.
10. R. N. Butler, F. L. Scott, T. A. F. O'Mahony, Chem. Rev. 1973, 73, 93; R. N. Butler, Chem. Rev. 1984, 84, 249; A. Kotali, Curr. Org. Chem. 2002, 6, 965.
11. R. N. Butler, F. L. Scott, T. A. F. O'Mahony, Chem. Rev. 1973, 73, 93; R. N. Butler, Chem. Rev. 1984, 84, 249; A. Kotali, Curr. Org. Chem. 2002, 6, 965.
12. M. Bekhazi, P. J. Smith, J. Warkentin, Can. J. Chem. 1984, 62, 1646; J. Warkentin, J. Chem. Soc., Perkin Trans. 1 2000, 2161; N. Merkley, J. Warkentin, Can. J. Chem. 2002, 80, 1187; W. Czardybon, A. Klys, J. Warkentin, N. H. Werstiuk, Can. J. Chem. 2003, 81, 1438.
13. M. Bekhazi, P. J. Smith, J. Warkentin, Can. J. Chem. 1984, 62, 1646; J. Warkentin, J. Chem. Soc., Perkin Trans. 1 2000, 2161; N. Merkley, J. Warkentin, Can. J. Chem. 2002, 80, 1187; W. Czardybon, A. Klys, J. Warkentin, N. H. Werstiuk, Can. J. Chem. 2003, 81, 1438.
14. M. Bekhazi, P. J. Smith, J. Warkentin, Can. J. Chem. 1984, 62, 1646; J. Warkentin, J. Chem. Soc., Perkin Trans. 1 2000, 2161; N. Merkley, J. Warkentin, Can. J. Chem. 2002, 80, 1187; W. Czardybon, A. Klys, J. Warkentin, N. H. Werstiuk, Can. J. Chem. 2003, 81, 1438.
15. M. Bekhazi, P. J. Smith, J. Warkentin, Can. J. Chem. 1984, 62, 1646; J. Warkentin, J. Chem. Soc., Perkin Trans. 1 2000, 2161; N. Merkley, J. Warkentin, Can. J. Chem. 2002, 80, 1187; W. Czardybon, A. Klys, J. Warkentin, N. H. Werstiuk, Can. J. Chem. 2003, 81, 1438.
16. T. J. Kealy, J. Am. Chem. Soc. 1962, 84, 966.
17. G. R. Pettit, D. C. Fessler, K. D. Paull, P. Hofer, J. C. Knight, J. Org. Chem. 1970, 35, 1398.
18. A. Stojiljković, N. Orbović, S. Sredojević, M. L. Mihailović, Tetrahedron 1970, 26, 1101; E. Ciganek, J. Org. Chem. 1965, 30, 4198; D. M. Gale, W. J. Middleton, C. G. Krespan, J. Am. Chem. Soc. 1965, 87, 657.
19. A. Stojiljković, N. Orbović, S. Sredojević, M. L. Mihailović, Tetrahedron 1970, 26, 1101; E. Ciganek, J. Org. Chem. 1965, 30, 4198; D. M. Gale, W. J. Middleton, C. G. Krespan, J. Am. Chem. Soc. 1965, 87, 657.
20. A. Stojiljković, N. Orbović, S. Sredojević, M. L. Mihailović, Tetrahedron 1970, 26, 1101; E. Ciganek, J. Org. Chem. 1965, 30, 4198; D. M. Gale, W. J. Middleton, C. G. Krespan, J. Am. Chem. Soc. 1965, 87, 657.