Metal-free diastereoselective synthesis of diaza-bicyclo[3.2.0]heptan-7-one and its transformation to functionalized proline esters

Tetrahedron Letters

Volumn 55, Issue 17, 2014, Pages 2793-2795

  Kumar, Yogesh ^a   Kuila, Bilash ^b   Mahajan, Dinesh ^b   Singh, Prabhpreet ^c   Mohapatra, Balaram ^d   Bhargava, Gaurav ^a  

^a I K GUJRAL PUNJAB TECHNICAL UNIVERSITY   (India)

^b Sphaerapharma Pvt Ltd   (India)

^c GURU NANAK DEV UNIVERSITY   (India)

^d INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

2 6 Diaza bicyclo 3.2.0 heptan 7 one; 3 Amino lactam; Halocyclization; Pyrrolidine ester

Indexed keywords

2 AZETIDINONE DERIVATIVE; 3 AMINO 2 AZETIDINONE; 4 HALO 3 ARYL AMINO PYRROLIDINE 2 CARBOXYLIC ACID METHYL ESTER; 4 HALO 3,6 DIARYL 2,6 DIAZA BICYCLO [3 2 0] HEPTAN 7 ONE; BICYCLO[3.2.0]HEPTANE DERIVATIVE; ESTER; METHOXIDE SODIUM; PROLINE DERIVATIVE; PROLINE ESTER DERIVATIVE; SODIUM DERIVATIVE; UNCLASSIFIED DRUG; ESTER DERIVATIVE; METAL; SODIUM;

AMINATION; ARTICLE; BIOTRANSFORMATION; CHEMICAL STRUCTURE; DIASTEREOISOMER; HALOAMINATION; CRYSTAL STRUCTURE; CYCLIZATION; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 84899096231     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.02.105     Document Type: Article

References (33)

1. B. Alcaide, P. Almendros, and C. Aragoncillo Chem. Rev. 107 2007 4437 4492 and reference cited therein
2. P. Singh, G. Bhargava, and M.P. Mahajan Tetrahedran Lett. 51 2010 4272 4274
3. P. Singh, R. Raj, G. Bhargava, D.T. Hendricks, S. Handa, L.G. Saughter, and V. Kumar Eur. J. Med. Chem. 2012 513
4. B. Alcaide, and P. Almendros Curr. Med. Chem. 11 2004 1921
5. A.R. Deshmukh, B.M. Bhawal, D. Krishnaswamy, V.V. Govande, B.A. Shinkr, and A. Jayanthi Curr. Med. Chem. 11 2004 1889
6. For recent syntheses of pyrrolidines: F.A. David, H. Xu, Y. Wu, and J. Zhang Org. Lett. 8 2006 2273
7. S. Cabrera, R.G. Arrayas, and J.C. Carretero J. Am. Chem. Soc. 127 2005 16394
8. F.A. Davis, H. Xu, Y. Wu, and J. Zhang Org. Lett. 8 2006 2273
9. J.L. Vasse, A. Joosten, C. Denhez, and J. Szymoniak Org. Lett. 7 2005 4887
10. J.W. Daly, T.F. Spande, and H.M. Garraffo J. Nat. Prod. 68 2005 1536
11. J.W. Daly, H.M. Garraffo, and T.F. Spande S.W. Pelletier, Alkaloid: Chemical and Biological Persprctives Vol 13 1999 Pergamon New York Chapter 1
12. B. List, A. Lerner, and C.F. Barbas III J. Am. Chem. Soc. 122 2000 2395
13. V.K. Aggarwal, C. Lopin, and F. Sandrinelli J. Am. Chem. Soc. 125 2003 7596
14. Y. Hayashi, T. Sumiya, J. Takahashi, H. Gotoh, T. Urushimaa, and M. Shoji Angew. Chem., Int. Ed. 45 2006 958
15. Chiral auxiliaries and ligand B.H. Kim, H.B. Lee, J.K. Hwang, and Y.G. Kim Tetrahedron: Asymmetry 16 2005 1215
16. F. Fache, E. Schultz, M.L. Tomasino, and M. Lemaire Chem. Rev. 100 2000 2159
17. For a review on the use of penicillin, see: D. Nathwani, and M.J. Wood Curr. Rev. Clin. Pharmacol. Ther. Drugs 45 1993 866
18. K.G. Holden R.B. Morin, M. Gorman, Chemistry and Biology of β-Lactam Antibiotics Vol. 2 1982 Academic London 114
19. T.D. Gootz Clin. Microbiol. Rev. 1990 13 31
20. F.J. Perez-Llarena, and G. Bou Curr. Med. Chem. 16 2009 3740
21. M. Shahid, F. Sobia, A. Singh, A. Malik, H.M. Khan, D. Jonas, and P.M. Hawkey Crit. Rev. Microbiol. 35 2009 81
22. G.A. Jacoby, and L.S.N. Munoz-Price Eng. J. Med. 352 2005 380
23. S. Paukner, L. Hesse, A. Prezelj, T. Solmajer, and U. Urleb Antimicrob. Agents Chemother. 53 2009 505
24. L.L. Silver Expert Opin. Ther. Patents 17 2007 1175
25. H. Chen, T.A. Blizzard, S. Kim, J. Wu, K. Young, Y.-W. Park, A.M. Ogawa, S. Raghoobar, R.E. Painter, D. Wisniewski, N. Hairston, P. Fitzgerald, N. Sharma, G. Scapin, J. Lu, J. Hermes, and M.L. Hammond Bioorg. Med. Chem. Lett. 21 2009 4267 4270 and reference cited therein
26. J.-P. Jacquet, D. Bouzard, J.-R. Kiechel, and P. Remuzon Tetrahedron Lett. 32 1991 1565
27. C. Napolitano, M. Borriello, F. Cardullo, D. Donati, A. Paio, and S. Manfredini Tetrahedron Lett. 50 2009 7280 7282
28. Schrimpf, M. R.; Tietjie, K. R.; Toupence, R. B.; Ji, J.; Basha, A.; Bunnelle, W. H.; Daanen, J. E.; Pace, J. M.; Sippy, K. B. International Patent WO0181347, 2001.
29. For synthesis of 3-amino2-azetidinone see: F.H. Van der Steen, and G.V. Koten Tetrahedron 47 1991 7503 7524 and reference cited therein
30. P.T. Parvatkar, P.S. Parameswaran, and S.G. Tilve Chem. Eur. J. 18 2012 5460 5489 and reference cited therein
31. For iodocyclization of unsaturated sulfites see: X.-F. Ren, E. Turos, C.H. Lake, and M.R. Churchill J. Org. Chem. 60 1995 6468 6483
32. S.S. Bari, A. Bhalla, Reshma, and G. Hundal Tetrahedran Lett. 54 2013 483 486
33. For rules of ring closure see: J.E. Baldwin Chem. Commun. 1976 734 736