3912
Y. Xu, S. Zhu / Tetrahedron 57 *2001) 3909±3913
concentrated to give a residue which was subject to silica
gel chromatography.
cm21 3245vs, 2986m,1714vs, 1458m, 1413s, 859,821m.
dH7CDCl3): 9.14 71H, br), 7.70 72H, d, J8.3), 7.34 72H,
d, J8.3), 3.24 73H, s), 2.44 73H, s), 1.29 76H, s). m/z 272
7M111, 6.05), 155 7Ts1, 2.60), 91 7C7H71, 8.99), 73
7M1-CONHTs, 100.00). 7Found: C, 53.15; H, 6.27; N,
5.17%. Calcd. For C12H17NO4S C, 53.14; H, 6.27; N,
5.16%.)
3.2.1. Methyl N-p-toluenesulfonyl glycinate )3a). Color-
less crystals, mp 92±38C, lit.11 92±38C. Structural data
agree with those of lit.
3.2.2. Ethyl N-p-toluenesulfonyl glycinate )3b). Colorless
crystals, mp 62±48C, lit.6 64±58C. Structural data agree
with those of lit.
3.2.9. 1-p-Toluenesulfonyl-2-methoxyl-2-trimethylsilyl-
oxy-3,3-dimethyl-aziridine )5e). White solid, mp 84±
58C. nmax 7KBr)/cm21 2973m, 1627vs, 1313s, 1149vs,
843,823m. dH7CDCl3): 7.86 72H, d, J8.1), 7.25 72H, d,
J8.1), 3.68 73H, s), 2.41 73H, s), 1.64 76H, s), 0.30 79H,
s). m/z 344 7M111, 2.13), 328 7M1-CH3, 25.73), 155 7Ts1,
12.69), 131 7C5H11O2Si1, 100.00), 91 7C7H71, 45.44).
7Found: C, 52.24; H, 7.34; N, 4.21%. Calcd. For
C15H25NO4SSi C, 52.48; H, 7.29; N, 4.08%.)
3.2.3. 2-Methoxyl-N-p-toluenesulfonyl propanamide )4c).
Colorless crystals, mp 62±48C. nmax 7KBr)/cm21 3167vs,
2985m,1716s, 1429s, 1375s, 858m. dH7CDCl3): 9.00 71H,
s), 7.97 72H, d, J8.5), 7.34 72H, d, J8.5), 3.72 71H, q,
J6.8), 3.36 73H, s), 2.44 73H, s), 1.30 73H, d, J6.8). m/z
227 7M111-OCH3, 1.84), 198 7M1-C3H7O, 2.87), 155
7Ts1, 6.29), 91 7C7H71, 20.77), 59 7C3H7O1, 100.00).
7Found: C, 51.17; H, 5.98; N, 5.25%. Calcd. For
C11H15NO4S C, 51.36; H, 5.84; N, 5.45%.)
3.2.10. Ethyl 2-methyl-N-p-toluenesulfonyl alaninate
)3f). Colorless crystals, mp 100±18C, lit.6 1018C. Structural
data agree with those of lit.
3.2.4. 1-p-Toluenesulfonyl-2-methoxyl-2-trimethylsilyl-
oxy-3-methyl-aziridine )5c). Colorless liquid. nmax 7KBr)/
cm21 2952m, 1607vs, 1315s, 1157s, 850m. dH7CDCl3): 7.68
72H, d, J8.2), 7.15 72H, d, J8.2), 5.33 71H, t, q 6.5), 3.60
73H, s), 2.27 73H, s), 1.34 73H, d, J6.5), 0.01 79H, s). m/z
7ESI): 331 7M112, 20.0), 330 7M111, 100.0). 7Found: C,
51.17; H, 7.00; N, 4.17%. Calcd. For C14H23NO4S C, 51.06;
H, 6.99; N, 4.26%.)
3.2.11. 2-Ethoxyl-2-methyl-N-p-toluenesulfonyl propan-
amide )4f). Colorless crystals, mp 107±1088C. nmax 7KBr)/
cm21 3275vs, 2983m,1714vs, 1465±1309vs, 1246s, 1178s.
dH7CDCl3): 9.10 71H, s), 7.95 72H, d, J8.3), 7.33 72H, d,
J8.3), 3.39 72H, q, J7.0), 2.43 73H, s), 1.29 76H, s), 1.22
73H, t, J7.0). m/z 286 7M111, 7.62), 240 7M1-OEt, 1.86),
155 7Ts1, 1.96), 91 7C7H71, 8.74), 87 7C5H11O1, 100.00).
7Found: C, 54.67; H, 6.76; N, 4.87%. Calcd. For
C13H19NO4S C, 54.74; H, 6.67; N, 4.91%.)
3.2.5. 2-Ethoxyl-N-p-toluenesulfonyl propanamide )4d).
Colorless crystals, mp 90±18C. nmax 7KBr)/cm21 3258vs,
2981m,1722s, 1438s, 1404vs, 822m. dH7CDCl3): 8.99 71H,
br), 7.97 72H, d, J8.3), 7.31 72H, d, 8.3), 3.59 71H, m),
3.45 71H, m), 2.44 73H, s), 1.30 73H, d±d, J6.8, 0.7), 1.23
73H, t, J6.1). m/z 272 7M111, 31.16), 155 7Ts1, 9.30), 91
7C7H71, 24.14), 73 7TMS1, 100.00), 45 7C2H5O1, 42.91).
7Found: C, 53.25; H, 6.32; N, 5.11%. Calcd. For
C12H17NO4S C, 53.14; H, 6.27; N, 5.17%.)
X-Ray diffraction analysis were performed from transparent
colorless crystals 4f. The cell parameters were determined
on the basis of 3162 re¯ections. The numbers of re¯ections
were obtained with Mo-Ka radiation and 2umax55.08
7graphite monochromator). Measurements were made on a
Rigaku AFC7R diffractometer. All calculations were
performed using the teXsan crystallographic software pack-
age of Molecular Structure Corporation. The programmes
SHELXS 86 were employed. The structures were solved by
direct methods and re®ned anisotropically by the full
matrix least squares method. The weighting scheme for
3.2.6. 1-p-Toluenesulfonyl-2-ethoxyl-2-trimethylsilyloxy-
3-methyl-aziridine )5d). Colorless liquid. nmax 7KBr)/cm21
2958m, 1599vs, 1376m, 1071vs, 850m. dH7CDCl3): 7.83
72H, d, J8.4), 7.31 72H, d, J8.4), 5.48 71H, q, J6.5),
4.19 72H, q, J7.1), 2.43 73H, s), 1.50 73H, d, J6.5), 1.30
73H, t, J7.1), 0.16 79H, s). m/z 343 7M1, 0.26), 328
7M1-CH3, 10.30), 270 7M1-TMS, 22.46), 188 7M1-Ts,
100.00), 155 7Ts1, 25.33), 91 7C7H71, 43.27), 73 7TMS1,
71.73). 7Found: C, 52.60; H, 7.43; N, 3.97%. Calcd. For
C15H25NO4SSi C, 52.48; H, 7.29; N, 4.08%.)
P
P
2
2
Rw w7uFou2uFcu)2/ wFo . The positions of hydrogen
atoms were calculated and included in the re®nement with
isotropic description. Crystal data: C13H19NO4S, mono-
clinic, space group, P21/n7#14), a8.51271), b10.96774),
Ê
Ê 3
c15.94674) A, b98.3772)8, V1473.976) A , Z4,
Dc1.290g. cm23
,
0.30 mm, re¯ection measured, 3162 independent intensities,
size of the crystal, 0.20£0.20£
2
2
2064 observed 7Fo .3s7Fo )), R0.041, Rw0.055.
3.2.7. Methyl 2-methyl-N-p-toluenesulfonyl alaninate )3e).
Colorless crystals, mp 94±58C nmax 7KBr)/cm21 3243vs,
2952m, 1734vs, 1431m, 1332s, 856,858m. dH7CDCl3):
7.76 72H, d, J8.3), 7.27 72H, d, J8.3), 5.42 71H, br),
3.66 73H, s), 2.42 73H, s), 1.47 76H, s). m/z 272 7M111,
0.34), 256 7M1-CH3, 0.60), 212 7M1-CO2Me, 100.00), 155
7Ts1, 54.13), 91 7C7H71, 81.33). 7Found: C, 51.15; H, 6.27;
N, 5.19%. Calcd. For C12H17NO4S C, 51.14; H, 6.27; N,
5.16%.)
The atomic coordinates, equivalent isotropic distropic
displacement parameters, lengths, bond angles, anisotropic
displacement parameters, H-atom coordinates and isotropic
displacementparamerts of compound 4f have been
deposited at Cambridge Crystallographic Data Center as
supplementary publication no. CCDC-149372.
3.2.12. 1-p-Toluenesulfonyl-2-ethoxyl-2-trimethylsilyloxy-
3,3-dimethyl-aziridine )5f). White solid, mp 107±88C. nmax
7KBr)/cm21 2954m, 1623vs, 1465m, 1327s, 848s.
dH7CDCl3): 7.83 72H, d, J8.2), 7.25 72H, d, J8.2), 4.04
3.2.8. 2-Methoxyl-2-methyl-N-p-toluenesulfonyl propan-
amide )4e). Colorless crystals, mp 107±88C. nmax 7KBr)/