Mechanistic insight into the spirocyclopropane isoxazolidine ring contraction

Organic Letters

Volumn 16, Issue 3, 2014, Pages 960-963

  Diethelm, Stefan ^a   Schoenebeck, Franziska ^b   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; OXAZOLE DERIVATIVE; OXAZOLIDINE; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; QUANTUM THEORY; SYNTHESIS;

BETA-LACTAMS; CATALYSIS; CYCLOPROPANES; MOLECULAR STRUCTURE; OXAZOLES; QUANTUM THEORY; SPIRO COMPOUNDS;

EID: 84893833072     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403693t     Document Type: Article

References (29)

1. Brandi, A.; Chicchi, S.; Cordero, F. M. Chem. Rev. 2008, 108, 3988
2. The Chemistry of β-lactams; Page, M. I., Ed.; Chapman & Hall: London, 1992.
3. Kvaerno, L.; Werder, M.; Hauser, H.; Carreira, E. M. J. Med. Chem. 2005, 48, 6035
4. Vandekerckhove, S.; D'hooghe, M. Bioorg. Med. Chem. 2013, 21, 3643
5. Cordero, F. M.; Pisaneschi, F.; Goti, A.; Ollivier, J.; Salaün, J.; Brandi, A. J. Am. Chem. Soc. 2000, 122, 8075
6. Cordero, F. M.; Pisaneschi, F.; Salvati, M.; Paschetta, V.; Ollivier, J.; Salaün, J.; Brandi, A. J. Org. Chem. 2003, 68, 3271
7. Diethelm, S.; Carreira, E. M. J. Am. Chem. Soc. 2013, 135, 8500
8. Adlington, R. M.; Baldwin, J. E.; Rawlings, B. J. J. Chem. Soc., Chem. Commun. 1983, 290
9. Pirrung, M. C. J. Am. Chem. Soc. 1983, 105, 7207
10. Baldwin, J. E.; Jackson, D. A.; Adlington, R. M.; Rawlings, B. J. J. Chem. Soc., Chem. Commun. 1985, 206
11. Pirrung, M. C. J. Org. Chem. 1987, 52, 4179
12. Cordero, F. M.; Vurchio, C.; Brandi, A.; Gandolfi, R. Eur. J. Org. Chem. 2011, 5608
13. Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 111, 230
14. Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 111, 2674
15. Avila, D. V.; Brown, C. E.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1993, 115, 466
16. Avila, D. V.; Brown, C. E.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1993, 115, 466
17. Brandi, A.; Guarna, A.; Goti, A.; Pericciuoli, F.; De Sarlo, F. Tetrahedron Lett. 1986, 27, 1727
18. All calculations were conducted with Gaussian09, Revision A.01; Frisch, M. J. See Supporting Information for full reference and further computational details.
19. Nendel, M.; Sperling, D.; Wiest, O.; Houk, K. N. J. Org. Chem. 2000, 65, 3259
20. Siebert, M. R.; Osbourn, J. M.; Brummond, K. M.; Tantillo, D. J. J. Am. Chem. Soc. 2010, 132, 11952
21. Northrop, B. H.; Houk, K. N. J. Org. Chem. 2006, 71, 3
22. Carpenter, B. K. Chem. Rev. 2013, 113, 7265
23. Cahard, E.; Schoenebeck, F.; Garnier, J.; Cutulic, S. P. Y.; Zhou, S.; Murphy, J. A. Angew. Chem., Int. Ed. 2012, 51, 3673
24. Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036
25. Cremer, D.; Filatov, M.; Polo, V.; Kraka, E.; Shaik, S. Int. J. Mol. Sci. 2002, 3, 604
26. Lee, T. J.; Rendell, A. P.; Taylor, P. R. J. Phys. Chem. 1990, 94, 5463
27. This is in line with a previous study by Ochoa et al. on the thermal rearrangement of spirocyclopropane isoxazolidines in the absence of a proton (Brandi reaction): Ochoa, E.; Mann, M.; Sperling, D.; Fabian, J. Eur. J. Org. Chem. 2001, 4223
28. Cox, C.; Lectka, T. Acc. Chem. Res. 2000, 33, 849
29. Atanasov, B. P.; Mustafi, D.; Makinen, M. W. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 3160