A novel enantiopure tricyclic β-lactam via stereoselective intramolecular nitrilimine cycloaddition

Tetrahedron Asymmetry

Volumn 21, Issue 21-22, 2010, Pages 2607-2611

  Buttero, Paola Del ^a   Molteni, Giorgio ^a   Pilati, Tullio ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 METHOXYPHENYL) 3 (1 HYDROXYCARBONYL)HYDROXY METHYLENE 4 [2 PHENYL]ETHYLIDENE AZETIDIN 2 ONE; 1 (4 METHOXYPHENYL) 3 (1 METOXYCARBONYL) HYDROXYMETHYLENE 4 [2 PHENYL]ETHYLIDENE AZETIDIN 2 ONE; 1 (4 METHOXYPHENYL) 3 (1 PHENYLCARBONYL) HYDROXYMETHYLENE 4 [2 PHENYL]ETHYLIDENE AZETIDIN 2 ONE; 1 (4 METHOXYPHENYL) 3 (2 CHLORO 2 PHENYL HYDRAZINIMINO) HYDROXYETHYLENE 4 [2 PHENYL]ETHYLIDENE AZETIDIN 2 ONE; 1 (4 METHOXYPHENYL) 3 ACETOXY 4 [2 PHENYL]ETHYLIDENE AZETIDIN 2 ONE; 1 (4 METHOXYPHENYL) 3 HYDROXY 4 [2 PHENYL]ETHYLIDENE AZETIDIN 2 ONE; 1,11 DIPHENYL 7 OXO 8 (4 METHOXYPHENYL) AZETO[3',4':2,3]PYRANO[4,5 C]PYRAZOLE; AZETIDINONE DERIVATIVE; TRIBACTAM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; ENANTIOSELECTIVITY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; STAUDINGER REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 78649853468     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.10.018     Document Type: Article

References (22)

1. E.L. Setti, and R.G. Micetich Curr. Med. Chem. 5 1998 101
2. G.I. Georg, and V.T. Rabikumar G.I. Georg, The Organic Chemistry of β-Lactams 1993 VCH New York
3. N.H. Cromwell, and B. Phillips Chem. Rev. 79 1979 331
4. V.P. Sandanayaka, and A.S. Prashad Curr. Med. Chem. 9 2002 1145
5. T.K. Ritter, and C.-H. Wong Angew. Chem., Int. Ed. 40 2001 3508
6. N. Díaz, D. Suárez, and K.M.M. Merz Jr. J. Am. Chem. Soc. 122 2000 4197
7. M.I. Page, The Chemistry of β-Lactams 1992 Chapman and Hall London
8. R.B. Morris, M. Gorman, Chemistry and Biology of β-Lactam Antibiotics 1982 Academic New York
9. B. Alcaide, and E. Sáez Eur. J. Org. Chem. 2005 1680
10. B. Alcaide, P. Almendros, J.M. Alonso, M.F. Aly, C. Pardo, E. Sáez, and M.R. Torres J. Org. Chem. 67 2002 7004
11. P. Del Buttero, and G. Molteni Tetrahedron: Asymmetry 17 2006 1319
12. P. Del Buttero, G. Molteni, and T. Pilati Tetrahedron 61 2005 2413
13. J.S. Prasad, and L.S. Liebeskind Tetrahedron Lett. 29 1988 4253
14. P. Wolkoff Can. J. Chem. 53 1975 1333
15. L. Bruché, G. Broggini, L. Garanti, and G. Zecchi J. Chem. Soc., Perkin Trans. 1 1994 403
16. T.J. Batterham NMR Spectra of Simple Heterocycles 1973 Wiley-Interscience New York p 206
17. As Implemented in the HyperChem 7.04 Professional Package of Programs; Hypercube Inc., 2002.
18. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.P. Stewart J. Am. Chem. Soc. 107 1985 3902
19. Crystallographic data (excluding structure factors) for structure (6S,9R,10R,11R)-9 have been deposited with the Cambridge Crystallographic data Centre as supplementary publication number CCDC 779769.
20. J.A. Carr, T.F. Al-Azemi, T.E. Long, J.-Y. Shim, C.M. Coates, E. Turos, and K.S. Bisht Tetrahedron 59 2003 9147
21. R. Brieva, J.Z. Crich, and C.J. Sih J. Org. Chem. 58 1993 1068
22. D.R. Kronenthal, C.Y. Han, and M.K. Taylor J. Org. Chem. 47 1982 2765