J. Blacker et al. / Tetrahedron: Asymmetry 17 (2006) 1449–1456
1455
762–766; Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai,
M.; Shibasaki, M. Angew. Chem., Int. Ed. 2000, 39, 1650–
1652; Kobayashi, S.; Ishitani, H. Chirality 2000, 12, 540–543;
Nogami, H.; Matsunaga, S.; Kanai, M.; Shibasaki, M.
Tetrahedron Lett. 2001, 42, 279–283; Masumoto, S.; Usuda,
H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc.
2003, 125, 5634–5635; Toru, T.; Sugimoto, M.; Sato, N.;
Nakamura, S. Tetrahedron: Asymmetry 2004, 15, 1513–1516;
Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron
Lett. 2004, 45, 3147–3151; Kato, N.; Suzuki, M.; Kanai, M.;
Shibasaki, M. Tetrahedron Lett. 2004, 45, 3153–3155.
10. Mansawat, W.; Bhanthumavin, W.; Vilaivan, T. Tetrahedron
Lett. 2003, 44, 3805–3808.
4.5. N-Allyl-N-trifluoroacetyl (S)-2-amino-phenyl-
acetonitrile8
To a sample of N-allyl-(S)-2-amino-phenylacetonitrile
(0.01 g, 5.85 · 10ꢀ5 mol) in dichloromethane (1 mL) was
added trifluoroacetic anhydride (0.018 g, 8.78 · 10ꢀ5 mol).
The resulting solution was stirred for 1 h, then the solvent
was removed in vacuo to give the trifluoroacetyl-protected
a-amino nitrile which was analysed without purification.
dH (CDCl3) 3.91 (1H, dd, J 6.0, 17.0 Hz, NCH2), 4.15
(1H, dd, J 4.7, 17.0 Hz, NCH2), 5.13 (1H, d, J 17.0 Hz,
CH@CH2), 5.19 (1H, d, J 10.2 Hz, CH@CH2), 5.66 (1H,
m, CH@CH2), 6.65 (1H, s, NCHCN), 7.4–7.5 (5H, m,
ArH); chiral GC conditions (c-CD butyryl column): initial
temperature 100 ꢁC, hold at initial temperature for 5 min
then ramp rate 3 ꢁC/min. tR 22.8 min (major) and
22.7 min (minor).
´
11. Chavarot, M.; Byrne, J. J.; Chavant, P. Y.; Vallee, Y.
Tetrahedron: Asymmetry 2001, 12, 1147–1150.
12. Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120,
5315–5316.
´
13. Byrne, J. J.; Chavarot, M.; Chavant, P.-Y.; Vallee, Y.
Tetrahedron Lett. 2000, 41, 873–876.
14. Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W.
G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am.
Chem. Soc. 1999, 121, 4284–4285; Porter, J. R.; Wirschun, W.
G.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am.
Chem. Soc. 2000, 122, 2657–2658; Josephsohn, N. S.; Kuntz,
K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc.
2001, 123, 11594–11599.
Acknowledgements
The authors thank EPSRC and NPIL, for studentships (to
L.A.C. and C.G.) and NPIL for financial support. Mass
spectra were recorded by the EPSRC national mass spec-
trometry service at the University of Wales, Swansea, and
use of the EPSRC’s Chemical Database Service at Dares-
bury is also gratefully acknowledged.
15. Banphavichit, V.; Mansawat, W.; Bhanthumavin, W.; Vilai-
van, T. Tetrahedron 2004, 60, 10559–10568.
16. For reviews of catalytic asymmetric Strecker reactions and
related processes, see: Yet, L. Angew. Chem., Int. Ed. 2001,
40, 875–877; Gro¨ger, H. Chem. Euro. J. 2001, 7, 5246–5251;
Gro¨ger, H. Chem. Rev. 2003, 103, 2795–2827; Spino, C.
Angew. Chem., Int. Ed. 2004, 43, 1764–1766.
References
17. Keith, J. M.; Jacobsen, E. N. Org. Lett. 2004, 6, 153–155.
18. Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M.
J. Am. Chem. Soc. 2000, 122, 6327–6328; Takamura, M.;
Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc.
2001, 123, 6801–6808; Funabashi, K.; Ratni, H.; Kanai, M.;
Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784–10785;
Ichikawa, E.; Suzuki, M.; Yabu, K.; Albert, M.; Kanai, M.;
Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 11808–11809.
19. For a review of the development and applications of catalysts
2 and 3, see: Achard, T. R. J.; Clutterbuck, L. A.; North, M.
Synlett 2005, 1828–1847.
20. Belokon, Y. N.; Caveda-Cepas, S.; Green, B.; Ikonnikov, N.
S.; Khrustalev, V. N.; Larichev, V. S.; Mosckalenko, M. A.;
North, M.; Orizu, C.; Taravov, V. I.; Tasinazzo, M.;
Timofeeva, G. I.; Yashkina, L. V. J. Am. Chem. Soc. 1999,
121, 3968–3973.
1. Rosenthaler, L. Biochem. Z. 1908, 14, 238–253.
2. For reviews see: North, M. Tetrahedron: Asymmetry 2003, 14,
147–176; Brunel, J.-M.; Holmes, I. P. Angew. Chem., Int. Ed.
2004, 43, 2752–2778.
3. For reviews see: Gregory, R. J. H. Chem. Rev. 1999, 99, 3649–
3682; Effenberger, F.; Forster, S.; Wajant, H. Curr. Opin.
Biotechnol. 2000, 11, 532–539; Griengl, H.; Schwab, H.;
Fechter, M. Trends Biotechnol. 2000, 18, 252–256; Sukuma-
ran, J.; Hanefeld, U. Chem. Soc. Rev. 2005, 34, 530–542.
4. Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M.
J. Am. Chem. Soc. 1996, 118, 4910–4911.
5. Becker, C.; Hoben, C.; Schollmeyer, D.; Scherr, G.; Kunz, H.
Eur. J. Org. Chem. 2005, 1497–1499.
6. Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120,
4901–4902; Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1,
157–160; Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867–
870; Liu, B.; Feng, X.; Chen, F.; Zhang, G.; Cui, X.; Jiang, Y.
Synlett 2001, 1551–1554; Jiao, Z.; Feng, X.; Liu, B.; Chen, F.;
Zhang, G.; Jiang, Y. Eur. J. Org. Chem. 2003, 3818–3826;
Huang, J.; Corey, E. J. Org. Lett. 2004, 6, 5027–5029;
Tsogoeva, S. B.; Yalalov, D. A.; Hateley, M. J.; Weckbecker,
C.; Huthmacher, K. Eur. J. Org. Chem. 2005, 4995–5000;
Berkessel, A.; Mukherjee, S.; Lex, J. Synlett 2006, 41–44; Ooi,
T.; Uematsu, Y.; Maruoka, K. J. Am. Chem. Soc. 2006, 128,
2548–2549; Rueping, M.; Sugiono, E.; Azap, C. Angew.
Chem., Int. Ed. 2006, 45, 2617–2619.
21. Belokon, Y. N.; Blacker, J.; Clutterbuck, L. A.; North, M.
Org. Lett. 2003, 23, 4505–4507.
22. Lundgren, S.; Wingstrand, E.; Penhoat, M.; Moberg, C.
J. Am. Chem. Soc. 2005, 127, 11592–11593.
23. Belokon, Y. N.; Gutnov, A. V.; Moskalenko, M. A.;
Yashkina, L. V.; Lesovoy, D. E.; Ikonnikov, N. S.; Larichev,
V. S.; North, M. Chem. Commun. 2002, 244–245; Belokon, Y.
N.; Carta, P.; Gutnov, A. V.; Maleev, V.; Moskalenko, M.
A.; Yashkina, L. V.; Ikonnikov, N. S.; Voskoboev, N. V.;
Khrustalev, V. N.; North, M. Helv. Chim. Acta 2002, 85,
3301–3312.
24. Belokon, Y. N.; Green, B.; Ikonnikov, N. S.; North, M.;
Tararov, V. I. Tetrahedron Lett. 1999, 40, 8147–
8150; Belokon, Y. N.; Green, B.; Ikonnikov, N. S.; North,
M.; Parsons, T.; Tararov, V. I. Tetrahedron 2001, 57, 771–
779.
7. Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124,
10012–10014.
8. Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem.,
Int. Ed. 2000, 39, 1279–1281.
9. Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem.,
Int. Ed. 1998, 37, 3186–3188; Ishitani, H.; Komiyama, S.;
Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122,
25. Tararov, V. I.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov,
N. S.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon, Y. N.
Chem. Commun. 1998, 387–388.