Enantioselective, NHC-catalyzed bicyclo-β-lactam formation via direct annulations of enals and unsaturated N-sulfonyl ketimines

Journal of the American Chemical Society

Volumn 130, Issue 2, 2008, Pages 418-419

  He, Ming ^a   Bode, Jeffrey W ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; CARBENOID; CYCLOPENTANE DERIVATIVE; IMINE; BICYCLO COMPOUND; CARBENE; DRUG DERIVATIVE; HYDROCARBON; METHANE; SULFUR AMINO ACID;

ANNULATION REACTION; ARTICLE; CATALYSIS; CATALYST; CONJUGATION; ENANTIOSELECTIVITY; PROTON TRANSPORT; STEREOCHEMISTRY; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS, SULFUR; BETA-LACTAMS; BICYCLO COMPOUNDS; CATALYSIS; HYDROCARBONS; METHANE; STEREOISOMERISM;

EID: 40149107472     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0778592     Document Type: Article

References (25)

1. (a) Davies, D. E.; Storr, R. C. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 7, pp 247-267.
2. (b) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Elsevier: Oxford, 1996; Vol. 1B, pp 536-574.
3. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437-4492.
4. (a) For an overview of catalytic, enantioselective methods, see: France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Acc. Chem. Res. 2004, 37, 594-600.
5. (b) For review on the synthesis of β-lactams, see: (a) Singh, G. S. Tetrahedron 2003, 59, 7631-7649.
6. (a) Doyle, M. P.; Kalinin, A. V. Synlett 1995, 1075-1076.
7. (b) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Brury, W. J.; Lectka, T. J. Am. Chem. Soc. 2000, 122, 7831-7832.
8. (c) Hodous, B.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578-1589.
9. (d) Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 4572-4573.
10. For recent highlights and reviews, see: (a) Zeitler, K. Angew. Chem., Int. Ed. 2005, 44, 7506-7510.
11. (b) Marion, N.; Díez-González, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988-3000.
12. For the first reports of this concept, see: (a) Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370-14371.
13. (b) Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205-6208.
14. Chiang, P.-C.; Kaeobamrung, J.; Bode, J. W. J. Am. Chem. Soc. 2007, 129, 3520-3521.
15. Nair was the first to document an NHC-catalyzed cyclopentene formation with achiral imidazolium salts: Nair, V.; Vellalath, S.; Poonoth, M.; Suresh, E. J. Am. Chem. Soc. 2006, 128, 8736-8737.
16. For selected aza-benzoin reactions, see: (a) Murry, J. A.; Frantz, D. E.; Soheili, A.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 9696-9697.
17. (b) Mennen, S. M.; Gipson, J. D.; Kim, Y. R.; Miller, S. J. J. Am. Chem. Soc. 2005, 127, 1654-1655.
18. (a) He, M.; Struble, J. R.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 8418-8420.
19. (b) For Diels-Alder reactions from α-chloro aldehydes, see: He, M.; Uc, G. J.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 15088-15089.
20. Sohn, S. S.; Bode, J. W. Org. Lett. 2005, 7, 3873-3876.
21. Although other N-sulfonyl imines also work, we have previously established that N-para-methoxybenzenesulfonyl imines are ideal for suppressing electrophilic inhibition of the NHC catalyst: He, M.; Bode, J. W. Org. Lett. 2005, 7, 3131-3134.
22. Both enantiomers of 1 are commercially available from Aldrich or BioBlocks, Inc. For the design and synthesis of related triazolium salts, see: (a) Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans. 1 1998, 1891-1894.
23. (b) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299.
24. In the NHC-catalyzed redox esterification of ynals, Zeiter has employed DMAP as the catalytic base: Zeitler, K. Org. Lett. 2006, 8, 637-640.
25. Non-chalcone-derived imines afforded only trace amounts of the β-lactam products due to diminished reactivity or instability of the imines. See the Supporting Information for examples.