Direct and diastereoselective alkylation and aldol reactions of α-bromo-α-fluoro-β-lactams

Journal of Organic Chemistry

Volumn 78, Issue 16, 2013, Pages 7903-7911

  Tarui, Atsushi ^a   Kawashima, Naoto ^a   Kawakita, Tetsuya ^a   Sato, Kazuyuki ^a   Omote, Masaaki ^a   Ando, Akira ^a  

^a SETSUNAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL REACTIONS; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE ALKYLATION; DIRECT ALKYLATION; ELECTROPHILES; FACILE ACCESS; OVERALL SCOPE; REACTION CONDITIONS;

ALKYLATION; CONDENSATION REACTIONS; STEREOSELECTIVITY;

AMIDES;

ALDEHYDE; ALPHA BROMO ALPHA FLUORO BETA LACTAM DERIVATIVE; BETA LACTAM DERIVATIVE; ELECTROPHILE; HALIDE; HALOGEN; HYDROGEN; KETONE; RADICAL; THIENAMYCIN; UNCLASSIFIED DRUG; ZINC;

ALDOL REACTION; ALKYLATION; ARTICLE; ARYLATION; CYCLOADDITION; DIASTEREOISOMER; ELECTROPHILICITY; FLUORINATION; FLUORINE NUCLEAR MAGNETIC RESONANCE; LOW TEMPERATURE; NUCLEAR OVERHAUSER EFFECT; POLYMERIZATION; STEREOCHEMISTRY;

ALKYLATION; BETA-LACTAMS; KETONES; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84882368867     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401072h     Document Type: Article

References (39)

1. Theodoridis, G. Adv. Fluorine Sci. 2006, 2, 121-175
2. O'Hagan, D. J. Fluorine Chem. 2010, 131, 1071-1081
3. O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308-319
4. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330
5. Jeschke, P. ChemBioChem 2004, 5, 570-589
6. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305-321
7. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475-4521
8. Turos, E.; Coates, C.; Shim, J.-Y.; Wang, Y.; Leslie, J. M.; Long, T. E.; Reddy, G. S. K.; Ortiz, A.; Culbreath, M.; Dickey, S.; Lim, D. V.; Alonso, E.; Gonzalez, J. Bioorg. Med. Chem. 2005, 13, 6289-6308
9. Galletti, P.; Giacomini, D. Curr. Med. Chem. 2011, 18, 4265-4283
10. Burnett, D. A.; Caplen, M. A.; Davis, H. A.; Burrier, R. E.; Clader, J. W. J. Med. Chem. 1994, 37, 1733-1736
11. Clader, J. W.; Burnett, D. A.; Caplen, M. A.; Domolski, M. S.; Dugar, S.; Vaccaro, W.; Sher, R.; Browne, M. E.; Zhao, H.; Burrier, R. E.; Salisbury, B.; Davis, H. A. J. Med. Chem. 1996, 39, 3684-3693
12. Dugar, S.; Yumibe, N.; Clader, J. W.; Vizziano, M.; Huie, K.; Heek, M. V.; Compton, D. S.; Davis, H. A. Bioorg. Med. Chem. Lett. 1996, 6, 1271-1274
13. McKittrick, B. A.; Ma, K.; Dugar, S.; Clader, J. W.; Davis, H. A.; Czarniecki, M. Bioorg. Med. Chem. Lett. 1996, 6, 1947-1950
14. Rosenblum, S. B.; Huynh, T.; Afonso, A.; Davis, H. A.; Yumibe, N.; Clader, J. W.; Burnett, D. A. J. Med. Chem. 1998, 41, 973-980
15. Rosenblum, S. B.; Huynh, T.; Afonso, A.; Davis, H. A. Tetrahedron 2000, 56, 5735-5742
16. Bateson, J. H.; Quinn, A. M.; Smale, T. C.; Southgate, R. J. Chem. Soc., Perkin Trans. 1 1985, 2219-2234
17. Kim, B. J.; Park, Y. S.; Beak, P. J. Org. Chem. 1999, 64, 1705-1708
18. Benfatti, F.; Cardillo, G.; Fabbroni, S.; Gentilucci, L.; Perciaccante, R.; Piccinelli, F.; Tolomelli, A. Synthesis 2005, 61-70
19. Dejaegher, Y.; Denolf, B.; Stevens, C. V.; Kimpe, N. D. Synthesis 2005, 193-198
20. Troisi, L.; Granito, C.; Pindinelli, E. Tetrahedron 2008, 64, 11632-11640
21. Madan, S.; Arora, R.; Venugopalan, P.; Bari, S. S. Tetrahedron Lett. 2000, 41, 5577-5581
22. Bari, S. S.; Venugopalan, P.; Arora, R. Tetrahedron Lett. 2003, 44, 859-897
23. Bhalla, A.; Rathee, S.; Madan, S.; Venugopalan, P.; Bari, S. S. Tetrahedron Lett. 2006, 47, 5255-5259
24. Bhalla, A.; Madan, S.; Venugopalan, P.; Bari, S. S. Tetrahedron 2006, 62, 5054-5063
25. Palomo, C.; Aizpura, J. M.; Ganboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223-3235
26. Van der Steen, F. H.; Van Koten, G. Tetrahedron 1991, 47, 7503-7524
27. Tada, K.; Toda, F. Tetrahedron Lett. 1978, 6, 563-564
28. Araki, K.; Wichtowski, J. A.; Welch, J. T. Tetrahedron Lett. 1991, 32, 5461-5464
29. Ishihara, T.; Ichihara, K.; Yamanaka, H. Tetrahedron 1996, 52, 255-262
30. Sekiguchi, T.; Sato, K.; Ishihara, T.; Konno, T.; Yamanaka, H. Chem. Lett. 2004, 33, 666-667
31. Jakowiecki, J.; Loska, R.; Makosza, M. J. Org. Chem. 2008, 73, 5436-5441
32. Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454-2462
33. Kawecki, R.; Welch, J. T. Tetrahedron Lett. 1993, 34, 3087-3090
34. Genêt, J.-P.; Durand, J.-O.; Roland, S.; Savignac, M.; Jung, F. Tetrahedron Lett. 1997, 38, 69-72
35. Tarui, A.; Kawashima, N.; Sato, K.; Omote, M.; Miwa, Y.; Minami, H.; Ando, A. Tetrahedron Lett. 2010, 51, 2000-2003
36. Tarui, A.; Kondo, S.; Sato, K.; Omote, M.; Minami, H.; Miwa, Y.; Ando, A. Tetrahedron 2013, 69, 1559-1565
37. Larsen, M.; Jørgensen, M. J. Org. Chem. 1996, 61, 6651-6655
38. Kondo, Y.; Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Lett. 2001, 3, 13-15
39. Mahrwald, R. Mordern Methods in Stereoselective Aldol Reactions; Weiey-VCH: Weinheim, 2013.