2522
V. G. Nenajdenko et al. / Tetrahedron: Asymmetry 12 (2001) 2517–2527
136.9, 137.0, 137.1 (C
Ts).
6
1-Ph, C
6
1-Ts, C
6
3-Th), 143.0 (C
6
4-
4.2.6.
N-[(1S)-1-(1-Benzothien-3-ylmethyl)-3-methyl-
butyl]-4-methylbenzenesulfonamide 6. White solid, yield
1.13 g (83%); mp 75–76°C; [Found: C, 65.14; H, 6.53.
C21H25NO2S2 requires: C, 65.08; H, 6.50%]; wmax/cm−1
3280 (NH); lH (400 MHz, CDCl3): 0.58 (3H, d, J=6.4
4.2.3.
N-[(1S)-2-(1-Benzothien-3-yl)-1-benzylethyl]-4-
methylbenzenesulfonamide 3. White solid, yield 0.93 g
(62%); mp 129–130°C; [Found: C, 68.41; H, 5.61.
C24H23NO2S2 requires: C, 68.38; H, 5.50%]; wmax/cm−1
Hz, CH2CH(CH3 2
CH2CH(CH3)2), 1.21–1.38 (2H, m, CH2
1.48–1.59 (1H, m, CH2CH(CH3)2), 2.26 (3H, s, CH3
Ts), 2.87–2.91 (2H, m, CH2
CHNH), 4.56 (1H, d, J=7.7 Hz, NH
CH-2Bth), 7.02 (2H, d, J=8.4 Hz, CH
7.27 (2H, m, 2CH
3,5-Ts), 7.52–7.55 (1H, d, CH
1CH-Bth); lC (100 MHz, CDCl3): 21.5 (C
22.8 (2C, CH2CH(CH3)2), 24.5 (CH2CH(CH3)2), 34.9
(CH2, a-Bth), 44.8 (CH2CH(CH3)2), 51.7 (CHNH),
121.6 (C4-Bth), 122.7 (C2-Bth), 123.8 (C7-Bth), 124.0
(C6-Bth), 124.1 (C5-Bth), 126.7 (C2, C6-Ts), 129.4 (C3,
5-Ts), 132.0 (C3-Bth), 137.3 (C1-Ts), 138.7 (C8-Bth),
140.4 (C9-Bth), 143.0 (C4-Ts).
6
) ), 0.77 (3H, d, J=6.4 Hz,
CH(CH3)2),
of
6
6
6
6
3250 (NH); lH (400 MHz, CDCl3): 2.20 (3H, s, CH3
Ts), 2.81–3.00 (4H, m, 2CH2), 3.54–3.64 (1H, m,
CHNH), 4.33 (1H, d, J=6.1 Hz, NH), 6.83 (1H, d,
J=8.2 Hz, CH-2,6-Ts), 6.98–7.04 (3H, m, CH-3,5-Ts,
1CH-Bth), 7.15–7.24 (7H, m, 5CH-Ph, 2CH-Bth), 7.33
(1H, d, J=7.9 Hz, CH-7Bth), 7.71 (1H, d, J=8.3 Hz,
CH-4Bth); lC (100 MHz, CDCl3): 21.4 (C
(CH2, a-Bth), 41.8 (CH2, a-Ph), 54.6 (C
(C4-Bth), 122.6 (C2-Bth), 123.9 (C
Bth), 126.3 (C3, C5-Ph), 126.6 (C5-Bth), 128.5 (C
6-Ts), 129.1 (C3, C5-Ts), 129.4 (C2, C6-Ph), 131.8
(C4-Ph), 136.1 (C3-Bth), 137.2 (C1-Ph), 138.3 (C1-Ts),
140.4 (C8-Bth), 142.5 (C9-Bth, C4-Ts).
6
of
6
, a-Bth), 3.46–3.54 (1H, m,
6
6
6
), 6.98 (1H, s,
6
6
6
6
-2,6-Ts), 7.23–
6
6
6
-Bth), 7.51 (2H, d, J=8.4 Hz, CH
-Bth), 7.71–7.74 (1H, m,
H3, Ts), 22.0,
6 -
6
6
6
6
6
6
6
6
6
H3, Ts), 33.7
HNH), 121.4
6
6
6
6
6
6
6
6
6
6
6
7-Bth), 124.0 (C
6
6-
2,
6
6
6
6
6
6
6
6
6
6
6
6
C
6
6
6
6
6
C
6
6
6
6
6
6
6
6
6
6
6
6
6
4.2.7. 4-Methyl-N-[(1S)-3-methyl-1-(1-naphtylmethyl)-
butyl]benzenesulfonamide 7. White oil, yield 0.97 g
(73%); [Found: C, 72.51; H, 7.17. C23H27NO2S requires:
C, 72.40; H, 7.13%]; wmax/cm−1 3260 (NH); lH (400
4.2.4.
4-Methyl-N-[(1S)-3-methyl-1-(2-thienylmethyl)-
butyl]benzenesulfonamide 4. Yellow oil, yield 0.79 g
(67%); [Found: C, 60.56; H, 6.90. C17H23NO2S2
requires: C, 60.50; H, 6.87%]; wmax/cm−1 3330 (NH); lH
(400 MHz, CDCl3): 0.61 (3H, d, J=6.6 Hz, CH2CH-
MHz, CDCl3): 0.47 (3H, d, J=6.6 Hz, CH2CH(CH3 2
0.74 (2H, d, J=6.6 Hz, CH2CH(CH3)2), 1.15–1.24 (1H,
m, CH2CH(CH3)2), 1.35–1.44 (1H, m, CH2CH(CH3)2),
1.51–1.61 (1H, m, CH2CH(CH3)2), 2.17 (3H, s, CH3 of
Ts), 2.95–3.02 (1H, m, CH2, a-Npht), 3.05–3.14 (1H, m,
CH2, a-Npht), 3.49–3.57 (1H, m, CHNH), 5.18 (1H, d,
J=5.7 Hz, NH), 6.89 (2H, d, J=8.5 Hz, CH-2,6-Ts),
7.08 (1H, d, J=6.0 Hz, CH-Npht), 7.18 (1H, dd, J=7.1
Hz, J=8.2 Hz, CH-Npht), 7.31–7.37 (2H, m, CH
Npht), 7.44 (2H, d, J=8.5 Hz, CH-3,5-Ts), 7.08 (1H, d,
J=8.2 Hz, CH-Npht), 7.64–7.68 (1H, m, CH-Npht),
7.77–7.81 (1H, m, 1CH-Npht); lC (100 MHz, CDCl3):
21.2 (CH3, Ts), 21.7, 22.8 (CH2CH(CH3)2), 24.2
(CH2CH(CH3)2), 39.6 (CH2,
(CH2CH(CH3)2), 52.4 (CHNH), 123.4 (C
(C8-Npht), 125.3 (C3-Npht), 125.8 (C
(C2, C6-Ts), 127.1 (C7-Npht), 127.8 (C
(C4-Npht), 129.0 (C3, C5-Ts), 131.7 (C
(C5-Npht), 133.8 (C10-Npht), 137.2 (C
Ts).
6 ) ),
6
6
6
(CH
(2H, t, J=7.2 Hz, CH2
CH2CH(CH3)2), 2.35 (3H, s, CH3
J=7.2 Hz, CH2-a-Th), 3.38–3.50 (1H, m, CH
(1H, d, J=8.4 Hz, NH), 6.62 (1H, d, J=0.9 Hz,
CH-3Th), 6.82 (1H, dd, J=0.9 Hz, J=1.2 Hz, CH
4Th), 7.04 (1H, d, J=1.2 Hz, CH-5Th), 7.22 (2H, d,
J=7.8 Hz, CH-2,6-Ts), 7.63 (2H, d, J=7.8 Hz, CH-3,5-
Ts); lC (100 MHz, CDCl3): 21.4 (CH3, Ts), 21.7, 22.7
(2C, CH2CH(CH3)2), 24.3 (CH2CH(CH3)2), 35.3 (CH2,
a-Th), 43.4 (CH2CH(CH3)2), 52.4 (CHNH), 124.3 (C5-
Th), 126.7 (C4-Th), 126.8 (C3-Th), 127.0 (C2, C6-Ts),
129.6 (C3, C5-Ts), 138.0 (C1-Ts), 138.5 (C2-Th), 143.2
(C4-Ts).
6
3)2), 0.72 (3H, d, J=6.6 Hz, CH2CH(CH3 2
CH(CH3)2), 1.45–1.58 (1H, m,
of Ts), 2.81 (2H, t,
NH), 4.52
6 ) ), 1.15
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6 -
6
6 -
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
a-Npht),
44.8
9-Npht), 125.1
6-Npht), 126.5
2-Npht), 128.5
6 1-Npht), 133.7
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
4.2.5.
4-Methyl-N-[(1S)-3-methyl-1-(3-thienylmethyl)-
6
6
6 1-Ts), 142.5 (C6 4-
butyl]benzenesulfonamide 5. White solid, yield 0.84 g
(71%); mp 74–75°C; [Found: C, 60.71; H, 6.98.
C17H23NO2S2 requires: C, 60.50; H, 6.87%]; wmax/cm−1
3240 (NH); lH (400 MHz, CDCl3): 0.62 (3H, d, J=6.9
4.2.8. N-[(1S)-1-Benzyl-3-methylbutyl]-4-methylbenzene-
sulfonamide 8. White solid, yield 0.88 g (76%); mp
73–74°C; [Found: C, 68.74; H, 7.58. C19H25NO2S
requires: C, 68.85; H, 7.60%]; wmax/cm−1 3230 (NH); lH
(400 MHz, CDCl3): 0.59 (3H, d, J=6.7 Hz,
Hz, CH2CH(CH3 2
CH2CH(CH3)2), 1.13
CH2CH(CH3)2), 1.45–1.55 (1H, m, CH2CH
2.36 (3H, s, CH3
J=6.0 Hz, CH2-a-Th), 2.69 (1H, dd, J=14.7 Hz, J=
6.2 Hz, CH2-a-Th), 3.39–3.49 (1H, m, CHNH), 4.24
(1H, d, J=8.2 Hz, NH), 6.72 (1H, dd, J=5.0 Hz,
J=1.0 Hz, CH-4Th), 6.79 (1H, dd, J=1.0 Hz, J=2.6
Hz, CH-2Th), 7.14 (1H, dd, J=5.0 Hz, J=2.6 Hz,
CH-5Th), 7.22 (2H, d, J=8.3 Hz, CH-2,6-Ts), 7.66
(2H, d, J=8.3 Hz, CH-3,5-Ts); lC (100 MHz, CDCl3):
21.5 (CH3, Ts), 21.8, 22.8 (2C, CH2CH(CH3)2), 24.4
(CH2CH(CH3)2), 35.7 (CH2,
(CH2CH(CH3)2), 52.1 (CHNH), 122.6 (C
(C5-Th), 127.0 (C2, C6-Ts), 128.8 (C
5-Ts), 136.9 (C3-Th), 138.0 (C1-Ts), 143.2 (C
6 ) ), 0.74 (3H, d, J=6.9 Hz,
6
(2H,
t,
J=6.5
Hz,
6
6
(CH3)2),
6
of Ts), 2.60 (1H, dd, J=14.7 Hz,
CH2CH(CH3 2
CH2CH(CH3)2), 1.11–1.17 (2H, m, CH2
1.47–1.55 (1H, m, CH2CH
Ts), 2.59–2.62 (2H, m, CH2
CHNH), 4.27 (1H, d, J=8.4 Hz, NH
J=8.4 Hz, CH-2,6-Ts), 7.11–7.21 (5CH
(2H, d, J=8.4 Hz, CH-3,5-Ts); lC (100 MHz, CDCl3):
21.5 (CH3, Ts), 21.7, 22.8 (2C, CH2CH(CH3)2), 24.3
(CH2CH(CH3)2), 41.6 (CH2,
(CH2CH(CH3)2), 52.9 (CHNH), 126.5 (C
(C2, C6-Ts), 128.4 (C2, C
129.7 (C3, C5-Ph), 137.0 (C1-Ph), 138.0 (C
(C4-Ts).
6
) ),
0.73
(3H,
d,
J=6.7
Hz,
6
6
6
CH(CH3)2),
6
6
6
(CH3)2), 2.34 (3H, s, CH3
, a-Ph), 3.38–3.48 (1H, m,
), 6.95 (2H, d,
, m, Ph), 7.63
6
of
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
a-Ph),
43.8
6
6
a-Th),
43.8
6
6
6
4-Ph), 127.0
6
6
6
2-Th), 125.6
4-Th), 129.6 (C
6
6
6
6
6-Ph), 129.6 (C
6 3, C6 5-Ts),
6
6
6
6
6
3,
6
6
6
6
1-Ts), 143.1
C
6
6
6
6
4-Ts).
6