7228
J. Han et al. / Tetrahedron Letters 47 (2006) 7225–7228
E. N. J. Am. Chem. Soc. 1993, 115, 5326; (c) Evans, D. A.;
N-(p-tolueneosulfonyl)-2-phenylaziridine (1) (382 mg, 70%
yield). 1H NMR (300 MHz, CDCl3): 7.88 (d, 2H,
J = 8.3 Hz), 7.22–7.36 (m, 7H), 3.80 (dd, 1H, J = 7.1,
4.5 Hz), 2.99 (d, 1H, J = 7.2 Hz), 2.45 (s, 3H), 2.41 (d, 1H,
J = 4.5 Hz); 13C NMR (75 MHz, CDCl3): 145.0, 135.4,
133.5, 130.2, 128.9, 128.7, 128.3, 126.9, 41.4, 36.3, 22.1; IR
(KBr): 3039, 3011, 2927, 1595, 1494, 1458, 1385, 1322,
Faul, M. M.; Anderson, B. A.; Barnes, D. M. J. Am.
Chem. Soc. 1993, 115, 5328; (d) Thakur, V. V.; Sudalai, A.
Tetrahedron Lett. 2003, 44, 989; (e) Llewellyn, D. B.;
Adamson, D. M.; Arndtsen, B. A. Org. Lett. 2000, 2,
4165; (f) Brandt, P.; Sodergren, M. J.; Andersson, P. A.;
Norrby, P. J. Am. Chem. Soc. 2000, 122, 8013; (g)
Gillespie, K. M.; Sanders, C. J.; O’Shaughnessy, P.;
Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem.
2002, 67, 3450.
1290, 1159, 1094, 909, 817, 714, 548 cmÀ1
.
Compounds 2–7 were synthesized with the same method
as for compound 1. N-(p-Toluenelsulfonyl)-2-(p-chloro-
phenyl)aziridine (2) (Table 2, entry 2). Obtained as white
9. (a) Sasaki, M.; Yudin, A. K. J. Am. Chem. Soc. 2003, 125,
14242; (b) Jain, S. L.; Sain, B. Tetrahedron Lett. 2003, 44,
575; (c) Sui, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124,
530; (d) Nishimura, M.; Minakata, S.; Takahashi, T.;
Oderaotoshi, Y.; Komatsu, M. J. Org. Chem. 2002, 67,
2101; (e) Hilt, R. Angew. Chem., Int. Ed. 2002, 41, 3586; (f)
Kano, D.; Minakata, S.; Komatsu, M. J. Chem. Soc.,
Perkin Trans. 1 2001, 3186; (g) Antunes, A. M. M.; Marto,
S. J. L.; Branco, P. S.; Prabhakar, S.; Lob, A. M. Chem.
Commun. 2001, 405; (h) Minakata, S.; Komatsu, M.
J. Synth. Org. Chem. Jpn. 2003, 61, 706.
10. (a) Saibabu Kotti, S. R. S.; Xu, X.; Wang, Y.; Headley, A.
D.; Li, G. G. Tetrahedron Lett. 2004, 45, 7209; (b) Wei, H.
X.; Kim, S. H.; Li, G. G. Tetrahedron 2001, 57, 3869; (c)
Chen, D. J.; Timmons, C.; Chao, S.; Li, G. G. Eur. J. Org.
Chem. 2004, 3097; (d) Li, G. G.; Wei, H. X.; Kim, S. H.;
Neighbors, M. Org. Lett. 1999, 1, 395.
1
solid. (336 mg, 55% yield). H NMR (300 MHz, CDCl3):
7.86 (d, 2H, J = 8.2 Hz), 7.34 (d, 2H, J = 8.0 Hz), 7.27 (d,
2H, J = 8.4 Hz), 7.15 (d, 2H, J = 8.4 Hz), 3.74 (dd, 1H,
J = 7.0, 4.4 Hz), 2.99 (d, 1H, J = 7.2 Hz), 2.45 (s, 3H),
2.35 (d, 1H, J = 4.4 Hz); 13C NMR (75 MHz, CDCl3):
145.2, 135.2, 134.5, 134.0, 130.2, 129.2, 128.3, 40.6, 36.45,
22.07; IR (KBr), 3003, 1594, 1492, 1374, 1323, 1302, 1161,
1092, 909, 814, 730, 552 cmÀ1
.
N-(p-Toluenelsulfonyl)-2-(p-bromophenyl)aziridine (3) (Table
2, entry 3). Obtained as white solid. (335 mg, 48% yield). 1H
NMR (300 MHz, CDCl3): 7.86 (d, 2H, J = 8.3 Hz), 7.42 (d,
2H, J = 8.4 Hz), 7.34 (d, 2H, J = 8.1 Hz), 7.09 (d, 2H,
J = 8.4 Hz),3.74 (dd, 1H, J = 7.1, 4.4 Hz), 2.99 (d, 1H,
J = 7.2 Hz), 2.45 (s, 3H), 2.35 (d, 1H, J = 4.4 Hz); 13C
NMR (75 MHz, CDCl3): 145.2, 135.2, 134.5, 132.1, 130.2,
128.6, 128.3, 122.7, 40.7, 36.4, 22.1; IR (KBr): 1593, 1488,
11. (a) Sopen, F. G. J. Chem. Soc. 1924, 125, 1899; (b)
Heintzelman, R. W.; Swern, D. Synthesis 1976, 731.
12. Karur, S.; Saibabu Kotti, S. R. S.; Xu, X.; Li, G. G.
J. Am. Chem. Soc. 2003, 125, 13340.
1454, 1371, 1320, 1301, 1160, 1092, 908, 813, 728, 551 cmÀ1
.
N-(p-Toluenelsulfonyl)-2,2-diphenylaziridine (4) (Table 2,
entry 4). Obtained as white solid. (510 mg, 73% yield). 1H
NMR (300 MHz, CDCl3): 7.71 (d, 2H, J = 7.3 Hz), 7.27–
7.39 (m, 12H), 3.10 (s, 2H), 2.44 (s, 3H); 13C NMR
(75 MHz, CDCl3): 144.4, 138.4, 136.9, 129.8, 129.2, 128.6,
128.5, 128.3, 57.4, 40.8, 22.02; IR (KBr): 3288, 3060, 3026,
1647, 1595, 1493, 1446, 1399, 1335, 1277, 1166, 1090, 957,
13. For some leading Pd-catalyzed aminations, see: (a) Wolfe,
J. P.; Tomori, H.; Yin, J.; Sadighi, J.; Buchwald, S. L. J.
Org. Chem. 2000, 65, 1158; (b) Wolfe, J. P.; Buchwald, S.
L. J. Org. Chem. 2000, 65, 1144; (c) Klapars, A.; Huang,
X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421; (d)
Singh, U. K.; Strieter, E. R.; Blackmond, D. I.; Buchwald,
S. L. J. Am. Chem. Soc. 2002, 124, 14104; (e) Nettekoven,
U.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 1166; (f)
Kawatsura, M.; Hartwig, J. F. Organometallics 2001, 20,
1960; (g) Lober, O.; Kawatsura, M.; Hartwig, J. F. J. Am.
Chem. Soc. 2001, 123, 4366; (h) Kawatsura, M.; Hartwig,
J. F. J. Am. Chem. Soc. 2000, 122, 9546.
858, 700, 544 cmÀ1
.
N-(p-Toluenelsulfonyl)-9-azabcyclo[6.1.0]nonane (5) (Table
2, entry 5). Obtained as white solid. (329 mg, 59% yield).
1H NMR (300 MHz, CDCl3): 7.81 (d, 2H, J = 8.3 Hz),
7.32 (d, 2H, J = 8.3 Hz), 2.78–2.80 (m, 1H), 2.45 (s, 3H),
1.99–2.05 (m, 1H), 1.31–1.59 (12H); 13C NMR (75 MHz,
CDCl3): 144.4, 136.2, 130.0, 127.9, 44.3, 26.8, 26.6, 25.6,
22.0; IR (KBr): 3069, 2954, 2926, 2855, 1598, 1497, 1450,
14. Kadota, I.; Shibuya, A.; Gyoung, Y. S.; Yamamoto, Y. J.
Am. Chem. Soc. 1998, 120, 10262.
1318, 1289, 1156, 1093, 932, 826, 725, 543 cmÀ1
.
Ethyl-4-(1-tosylaziridin-2-yl)benzoate (6) (Table 2, entry
6). Obtained as white solid (441 mg, 64% yield)
(C18H19NO4S, M = 345.3); Calcd: C, 62.61; H, 5.25.
Found: C, 62.39; H, 5.08; mp 87–88 ꢁC; 1H NMR
(300 MHz, CDCl3): 7.96 (d, 2H, J = 8.3 Hz), 7.86 (d, 2H,
J = 8.3 Hz), 7.33 (d, 2H, J = 8.0 Hz), 7.28 (d, 2H,
J = 8.2 Hz), 4.35 (q, 2H, J = 7.1 Hz), 3.80 (dd, 1H,
J = 7.1, 4.3 Hz), 3.02 (d, 1H, J = 7.2 Hz), 2.45 (s, 3H),
2.39 (d, 1H, J = 4.3 Hz), 1.38 (t, 3H, J = 7.1 Hz); 13C
NMR (75 MHz, CDCl3): 166.5, 145.3, 140.4, 135.1, 130.8,
130.2, 128.3, 126.9, 61.5, 40.9, 36.6, 22.0, 14.7; IR (KBr):
3036, 2987, 2906, 1706, 1607, 1481, 1446, 1365, 1329, 1285,
15. N-(p-Toluenesulfonyl)-2-phenylaziridine (1) (Table 2,
entry 1). Into a dry Schlenk tube or any capped vial of
an appropriate size was added styrene (312 mg, 3.0 mmol)
and freshly distilled DMF (2 mL). The reaction vial was
immersed in a room temperature bath with stirring under
an argon atmosphere. Then potassium carbonate (304 mg,
2.2 mmol) and palladium acetate (8.9 mg, 2 mol %) were
added. After stirring for 5 min, solid TsNCl2 (480 mg,
2 mmol) was added into the mixture. The resulting
mixture was stirred at room temperature for 24 h. After
completion of the reaction, it was quenched by addition of
H2O (15 mL). The aqueous solution was extracted with
ethyl acetate (3 · 20 mL). The combined organic layers
were washed with brine, dried over anhydrous sodium
sulfate, and concentrated. Purification by preparative TLC
plate (EtOAc/ petroleum ether = 5:1) provided white solid
1163, 1103, 908, 831, 720, 551 cmÀ1
. MS (ESMS/
[M+Na]+) Calcd for C18H19NO4SNa: 368.1. Found:
368.1. 1H NMR and 13C NMR spectra of compounds
2–5 and 7 of Table 1 have been confirmed to be identical to
those of known samples.5b