1. For a monograph, see: Aziridines and Epoxides in Organic
Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim,
2006.
2. For recent reviews, see: Olsen, C. A.; Franzyk, H.;
Jaroszewski, J. W. Eur. J. Org. Chem. 2007, 1717–1724;
Hu, X. E. Tetrahedron 2004, 60, 2701–2743; Sweeney, J. B.
Chem. Soc. Rev. 2002, 31, 247–258; McCoull, W.; Davis,
F. A. Synthesis 2000, 1347–1365.
3. Hodgkinson, T. J.; Kelland, L. R.; Shipman, M.; Vile, J.
Tetrahedron 1998, 54, 6029–6034.
4. Hediger, M. E. Bioorg. Med. Chem. 2004, 12, 4995–5010.
5. Goujon, J.-Y.; Gueyrard, D.; Compain, P.; Martin, O. R.;
Ikeda, K.; Kato, A.; Asano, N. Bioorg. Med. Chem. 2005,
13, 2313–2324.
6. Banwell, M. G.; Lupton, D. W.; Willis, A. C. Aust. J.
Chem. 2005, 58, 722–737.
7. Guo, Z. H.; Schultz, A. G. Tetrahedron Lett. 2004, 45,
919–921.
8. Kim, S.; Lee, Y. M.; Lee, J.; Lee, T.; Fu, Y.; Song, Y.;
Cho, J.; Kim, D. J. Org. Chem. 2007, 72, 4886–4891.
9. Wu, X.; Toppet, S.; Compernolle, F.; Hoornaert, G. J.
Tetrahedron 2003, 59, 1483–1491.
10. Chen, G.; Sasaki, M.; Li, X.; Yudin, A. K. J. Org. Chem.
2006, 71, 6067–6073.
11. For recent examples, see: Alves, M. J.; Fortes, A. G.;
Lemos, A.; Martins, C. Synthesis 2005, 555–558; Timen,
A. S.; Somfai, P. J. Org. Chem. 2003, 68, 9958–9963;
Davis, F. A.; Wu, Y.; Yan, H.; Prasad, K. R.; McCoull,
W. Org. Lett. 2002, 4, 655–658.
12. Ittah, Y.; Sasson, Y.; Shahak, I.; Tsaroom, S.; Blum, J. J.
Org. Chem. 1978, 43, 4271–4273.
13. The synthesis of the 1-azabicyclo[3.1.0]hexane skeleton of
ficellomycin has been achieved using a related approach,
see: Paumier, D.; Garcia, M.; Shipman, M.; Muir, J. C.
Synlett 2004, 2212–2214.
14. Prepared by oxidation of 5-hexen-1-ol (PCC, CH2Cl2,
18 h, rt), and used directly in the olefination reaction
without purification. For full details, see Supplementary
data.
15. Hiebl, J.; Kollmann, H.; Rovenszky, F.; Winkler, K. J.
Org. Chem. 1999, 64, 1947–1952.
16. The crude NH aziridine was partially characterised (1H
NMR and LRMS). However, attempts to purify it by
column chromatography on silica resulted in cyclisation to
1.
17. The (2S*,6S*)-stereochemistry of 1 was deduced by NOE
measurements (500 MHz, CDCl3). Specifically, strong
reciprocal enhancements were seen between H-2 and H-7
[H-2!H-7: 3.8%; H-7!H–2: 4.4%]. Irradiation of H-70
produced enhancements of H-6 (1.7%) and H-7 (9.7%).
No NOEs between H-2 and H-6 were observed. These
observations confirm a syn-relationship between the aziridine
ring and H-2.
18. Crystallographic data (excluding structure factors) for 6
have been deposited with the Cambridge Crystallographic
Data Centre as supplementary publication no. CCDC
658615. Copies of the data can be obtained, free of charge,
on application to CCDC, 12 Union Road, Cambridge
CB2 1EZ, UK, (fax: +44 0 1223 336033 or e-mail:
deposit@ccdc.cam.ac.uk).
19. For cyclisations involving simple x-amino alkenes. See,
for example, Banwell, M. G.; Bissett, B. D.; Bui, C. T.;
Pham, H. T. T.; Simpson, G. W. Aust. J. Chem. 1998, 51,
9–18; Knapp, S.; Hale, J. J. J. Org. Chem. 1993, 58, 2650–
2651; Knouzi, N.; Vaultier, M.; Toupet, L.; Carrie, R.
Tetrahedron Lett. 1987, 28, 1757–1760.
20. For a review, see: Laschat, S.; Dickner, T. Synthesis 2000,
1781–1813.