trans-1-Benzyl-2-(4-chlorophenyl)-3-(methoxymethyl)aziridine 7
4 (a) T. Manaka, S.-I. Nagayama, W. Desadee, N. Yajima, T. Kumamoto,
T. Watanabe, T. Ishikawa, M. Kawahata and K. Yamaguchi, Helv.
Chim. Acta, 2007, 90, 128; (b) K. Ishii, T. Sone, T. Shigeyama, M.
Noji and S. Sugiyama, Tetrahedron, 2006, 62, 10865; (c) P. Davoli,
E. Caselli, M. Bucciarelli, A. Forni, G. Torre and F. Prati, J. Chem.
Soc., Perkin Trans. 1, 2002, 1948; (d) P. Davoli, A. Forni, I. Moretti, F.
Prati and G. Torre, Tetrahedron, 2001, 57, 1801; (e) D. Tanner, H. T.
Korno, D. Guijarro and P. G. Andersson, Tetrahedron, 1998, 54, 14213;
(f) P. G. Andersson, D. Guijarro and D. Tanner, J. Org. Chem., 1997,
62, 7364; (g) A. L. Schwan and M. D. Refvik, Tetrahedron Lett., 1993,
34, 4901; (h) P. Baret, A. Boucherle, H. Handel, A. Million, J. L. Pierre,
A. Stenger, M. Charveron and H. Lauressergues, Eur. J. Med. Chem.,
1977, 12, 149.
Major invertomer. 1H NMR (300 MHz, CDCl3): d 2.39–2.44
(1H, m); 3.19 (1H, d, J = 3.3 Hz); 3.40 (3H, s); 3.71 (1H, d,
J = 14.3 Hz); 3.78–3.81 (2H, m); 4.12 (1H, d, J = 14.3 Hz);
7.17–7.36 (9H, m).13C NMR (75 MHz, CDCl3): d 44.32, 46.12,
55.53, 58.60, 68.52, 126.76, 127.57, 128.30, 128.40, 131.60, 132.53,
138.57, 139.67. IR (ATR cm-1): nmax = 2923, 2873, 2853, 1493,
1452, 1104, 1090, 802, 732, 696. MS (70 eV): m/z (%) 288/90
(M+ + 1, 100). Rf 0.25 (Et2O–hexane 1/1).
Minor invertomer. 1H NMR (300 MHz, CDCl3): d 2.39–2.44
(1H, m); 2.57 (1H, d, J = 2.8 Hz); 3.36 (3H, s); 3.55 (2H, d, J =
4.4 Hz); 3.71 and 4.12 (2 ¥ 1H, 2 ¥ d, J = 14.3 Hz); 7.17–7.36 (9H,
m).13C NMR (75 MHz, CDCl3): d 42.46, 44.08, 55.82, 58.87, 74.29,
126.83, 127.57, 127.98, 128.22, 128.30, 132.10, 133.87, 139.17. IR
(ATR, cm-1): nmax = 2923, 2873, 2853, 1493, 1452, 1104, 1090,
802, 732, 696. MS (70 eV): m/z (%) 288/90 (M+ + 1, 100). Rf 0.25
(Et2O–hexane 1/1).
5 T. W. Glinka, D. E. Shuster, C. S. Celly, R. D. Simmons and J. Zhang,
U.S. Pat., 2007, US 2007155799 A1; Chem. Abstr., 2007, 147, 143130.
6 A. Dagan, S. Gatt and S. Slavin, PCT Int. Appl., 2009, WO 2009060445
A1; Chem. Abstr., 2009, 150, 487727.
7 P. C. Anderson, T. Halmos, G. L. Jung, M.-A. Poupart and B.
Simoneau, U.S. Pat., 1996, US 5523315 A1; Chem. Abstr., 1996, 125,
142714.
8 G. Camaggi, D. Chiarino, M. Fantucci and G. Meazza, Eur. Pat., 1991,
EP 454067 A1; Chem. Abstr., 1992, 117, 48113.
9 (a) I. Ojima and F. Delaloge, Chem. Soc. Rev., 1997, 26, 377; (b) I.
Ojima, Acc. Chem. Res., 1995, 28, 383; (c) J. F. Fisher, S. O. Meroueh
and S. Mobashery, Chem. Rev., 2005, 105, 395; (d) B. Alcaide and
P. Almendros, Synlett, 2002, 381; (e) G. S. Singh, Tetrahedron, 2003,
59, 7631; (f) S. France, A. Weatherwax, A. E. Taggi and T. Lectka,
Acc. Chem. Res., 2004, 37, 592; (g) B. Alcaide, P. Almendros and
C. Aragoncillo, Chem. Rev., 2007, 107, 4437.
Anal. Calcd for C17H18ClNO: C 70.95, H 6.30, N 4.87. Found:
C 70.72, H 6.57, N 4.93%.
cis-1-tert-Butyl-2-(2-fluorophenyl)-3-(methoxymethyl)aziridine 9
10 (a) M. D’hooghe, W. Van Brabandt, S. Dekeukeleire, Y. Dejaegher and
N. De Kimpe, Chem.–Eur. J., 2008, 14, 6336; (b) M. D’hooghe, S.
Dekeukeleire and N. De Kimpe, Org. Biomol. Chem., 2008, 6, 1190;
(c) W. Van Brabandt, R. Van Landeghem and N. De Kimpe, Org. Lett.,
2006, 8, 1105; (d) W. Van Brabandt, Y. Dejaegher, R. Van Landeghem
and N. De Kimpe, Org. Lett., 2006, 8, 1101; (e) E. Boros, F. Bertha, G.
Czira, A. Feller, J. Fetter, M. Kajtar-Peredy and G. Simig, J. Heterocycl.
Chem., 2006, 43, 87; (f) Y. Dejaegher and N. De Kimpe, J. Org. Chem.,
2004, 69, 5974; (g) Y. Dejaegher, S. Mangelinckx and N. De Kimpe,
J. Org. Chem., 2002, 67, 2075; (h) S. Yamamoto, A. Kanetsuki, Y.
Sueishi and N. Nishimura, Bull. Chem. Soc. Jpn., 1990, 63, 2911;
(i) D. Johnson and H. Suschitzky, J. Chem. Soc., Perkin Trans. 1, 1976,
1062.
1H NMR (300 MHz, CDCl3): d 1.08 (9H, s); 2.28 (1H, d ¥ d ¥ d,
J = 6.1, 6.1, 5.9 Hz); 3.02 (1H, d, J = 6.1 Hz); 3.05 and 3.13 (2 ¥
1H, 2 ¥ (d ¥ d), J = 10.6, 6.1, 5.9 Hz); 3.19 (3H, s); 6.96–7.02, 7.05–
7.10, 7.16–7.23 and 7.46–7.51 (4 ¥ 1H, 4 ¥ m). 19F NMR (282 MHz,
CDCl3): d (-119.11)–(-119.03) (m). 13C NMR (75 MHz, CDCl3):
d 26.70, 32.93 (d, J = 3.4 Hz), 37.53, 53.07, 58.64, 71.41, 114.60
(d, J = 20.7 Hz), 123.56 (d, J = 3.5 Hz), 125.31 (d, J = 13.9 Hz),
128.02 (d, J = 8.1 Hz), 130.01 (d, J = 4.6 Hz), 161.88 (d, J =
245.8 Hz). IR (ATR, cm-1): nmax = 2962, 2924, 2855, 1491, 1455,
1241, 1222, 1138, 1107, 1096, 757. MS (70 eV): m/z (%) 238 (M+ +
1, 100). Rf 0.41 (hexane–EtOAc 9/1). Anal. Calcd for C14H20FNO:
C 70.86, H 8.49, N 5.90. Found: C 71.05, H 8.64, N 5.82%.
11 B. Van Driessche, W. Van Brabandt, M. D’hooghe, Y. Dejaegher and
N. De Kimpe, Tetrahedron, 2006, 62, 6882.
12 (a) K. D. Barrow and T. M. Spotswood, Tetrahedron Lett., 1965, 6,
3325; (b) J. Decazes, J. L. Luche and H. B. Kagan, Tetrahedron Lett.,
1970, 11, 3361.
13 (a) J. Xu, Arkivoc, 2009, (ix), 21; (b) L. Jiao, Y. Liang and J. X. Xu,
J. Am. Chem. Soc., 2006, 128, 6060.
Acknowledgements
14 (a) B. Li, Y. Wang, D.-M. Du and J. Xu, J. Org. Chem., 2007, 72, 990;
(b) Y. Wang, Y. Liang, L. Jiao, D.-M. Du and J. Xu, J. Org. Chem.,
2006, 71, 6983.
The authors are indebted to Ghent University (GOA) and the
Fund for Scientific Research-Flanders (FWO-Vlaanderen) for
financial support.
15 (a) K. D. Barrow and T. M. Spotswood, Tetrahedron Lett., 1965, 6,
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