3-benzyl-3-azabicyclo[3.1.1]heptan-6-one: A promising building block for medicinal chemistry

Organic Letters

Volumn 12, Issue 19, 2010, Pages 4372-4375

  Denisenko, Aleksandr V ^a   Mityuk, Andrey P ^a   Grygorenko, Oleksandr O ^a   Volochnyuk, Dmytro M ^a,c   Shishkin, Oleg V ^b   Tolmachev, Andrey A ^a   Mykhailiuk, Pavel K ^a  

^a ENAMINE LTD   (Ukraine)

^b TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^c INSTITUTE OF HYDROBIOLOGY   (Ukraine)

Author keywords

[No Author keywords available]

Indexed keywords

3 BENZYL 3 AZABICYCLO(3.1.1)HEPTAN 6 ONE; 3-BENZYL-3-AZABICYCLO(3.1.1)HEPTAN-6-ONE; BENZYL DERIVATIVE; BICYCLO COMPOUND; HEPTANE;

ARTICLE; CHEMICAL STRUCTURE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BENZYL COMPOUNDS; BICYCLO COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; HEPTANES; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 77957109994     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101866x     Document Type: Article

References (32)

1. Mann, A. Conformational restriction and/or steric hindrance in medicinal chemistry. In The Practice of Medicinal Chemistry, 3 rd ed.; Wermuth, C. G., Ed.; Academic Press/Elsevier: Amsterdam, 2008; p 363.
2. Martin, S. F. Pure Appl. Chem. 2007, 79, 193
3. Feher, M.; Schmidt, J. M. J. Chem. Inf. Comput. Sci. 2003, 43, 218
4. Cowell, S. M.; Lee, Y. S.; Cain, J. P.; Hruby, V. J. Curr. Med. Chem. 2004, 11, 2785
5. Komarov, I. V.; Grigorenko, A. O.; Turov, A. V.; Khilya, V. P. Russ. Chem. Rev. 2004, 73, 785
6. Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. 2003, 32, 1244
7. Grauer, A.; Knig, B. Eur. J. Org. Chem. 2009, 30, 5099
8. Vagner, J.; Qu, H.; Hruby, V. J. Curr. Opin. Chem. Biol. 2008, 12, 292
9. Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441
10. Kessler, H. Angew. Chem., Int. Ed. 1982, 94, 509
11. Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645
12. Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2009, 20, 1
13. Brackmann, F.; de Meijere, A. Chem. Rev. 2007, 37, 4493
14. Brackmann, F.; de Meijere, A. Chem. Rev. 2007, 37, 4538
15. Trabocchi, A.; Scarpi, D.; Guarna, A. Amino Acids 2008, 34, 1
16. Kubyshkin, V. S.; Mikhailiuk, P. K.; Komarov, I. V. Tetrahedron Lett. 2007, 48, 4061
17. Kubyshkin, V.; Mykhailiuk, P.; Ulrich, A.; Komarov, I. Synthesis 2009, 19, 3327
18. Tkachenko, A. N.; Radchenko, D. S.; Mykhailiuk, P. K.; Grygorenko, O. O.; Komarov, I. V. Org. Lett. 2009, 11, 5674
19. Wishart, D. S.; Knox, C.; Guo, A. C.; Cheng, D.; Shrivastaya, S.; Tzur, D.; Gautam, B.; Hassanali, M. Nucleic Acids Res. 2008, 36 (Database issue) D901
20. Earle, M. J.; Fairhurst, R. A.; Heaney, H.; Papageorgiou, G.; Wilkins, R. F. Tetrahedron Lett. 1990, 31, 4229
21. Heaney, H.; Papageorgiou, G. Tetrahedron 1996, 52, 3473
22. Halliday, J. I.; Chebib, M.; Turner, P.; McLeod, M. D. Org. Lett. 2006, 8, 3399
23. McLeod, M. D.; Halliday, J. I.; Chebib, M. WO2007/051255, 2007.
24. Nippon Soda Co. EP2058303, 2009.
25. Darout, E.; Basak, A. Tetrahedron Lett. 2010, 51, 2998
26. Mityuk, A. P.; Denisenko, A. V.; Dacenko, O. P.; Grygorenko, O. O.; Mykhailiuk, P. K.; Volochnyuk, D. M.; Shishkin, O. V.; Tolmachev, A. A. Synthesis 2010, 3, 493
27. For the reactions of N, N -bis(alkoxymethyl)alkylamine reagents with another ketones, see
28. Brocke, C.; Brimble, M. A.; Lin, D. S.-H.; McLeod, M. D. Synlett 2004, 13, 2359
29. Brimble, M. A.; Brocke, C. Eur. J. Org. Chem. 2005, 2385
30. Buckley, B. R.; Bulman Page, P. C.; Heaney, H.; Sampler, E. P.; Carley, S.; Brocke, C.; Brimble, M. A. Tetrahedron 2005, 61, 5876
31. Chan, Y.; Guthmann, H.; Brimble, M.; Barker, D. Synlett 2008, 17, 2601
32. Krishnamurti, R.; Bellew, D. R.; Prakash, G. K. S. J. Org. Chem. 1991, 56, 984