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X. Franck et al.
PAPER
and 0.2 mL, 2 mmol for 5). The mixture was stirred for 10 min and
the appropriate aldehyde (1.2 mmol) was added. After 30 min,
NH4Cl was added and the mixture was extracted with Et2O (2 × 20
mL). The combined Et2O layers were washed with aq 1 M HCl (10
mL), H2O (20 mL) and brine (20 mL), dried (MgSO4) and concen-
trated. The crude mixture was purified by flash chromatography
(CH2Cl2–cyclohexane, 9:1) to give pure aldols 6 and 7, respectively.
1H NMR (300 MHz, CDCl3): d = 0.84 (t, J = 7.3 Hz, 3 H), 1.34 (m,
2 H), 1.97 (m, 2 H), 2.70 (br s, 1 H, OH), 3.99 (dd, J = 8.2, 7.9 Hz,
1 H), 4.50 (dd, J = 9.2, 3.6 Hz, 1 H), 4.80 (dd, J = 9.0, 9.1 Hz, 1 H),
5.42 (dd, J = 15.4, 6.9 Hz, 1 H), 5.69 (m, 2 H), 6.06 (d, J = 9.2 Hz,
1 H), 6.84 (d, J = 7.9 Hz, 2 H), 7.03 (dd, J = 7.7, 7.6 Hz, 2 H), 7.25
(m, 1 H), 4.45 (m, 5 H).
13C NMR (75 MHz, CDCl3): d = 184.4, 168.2, 138.1, 137.1, 135.4,
129.0, 128.9, 128.7, 127.5, 126.8, 123.6, 73.4, 68.9, 61.8, 48.6,
34.1, 21.8, 13.4.
(2R,3S)-3-Hydroxy-3-phenyl-2-phenylselanyl-1-[(4R)-4-phe-
nyl-2-thioxooxazolidin-3-yl]propan-1-one (6a)
[a]D24 –279 (c 0.305, CHCl3).
Anal. Calcd for C23H25NO3SSe: C, 58.22; H, 5.31; N, 2.95; S, 6.76.
Found: C, 58.23; H, 5.33; N, 2.91; S, 6.67.
IR (KBr): 3470, 3030, 1690, 1370, 1350, 1185, 755, 700 cm–1.
1H NMR (300 MHz, CDCl3): d = 3.04 (br s, 1 H, OH), 4.42 (dd,
J = 9.2, 3.5 Hz, 1 H), 4.55 (dd, J = 9.2, 1.3 Hz, 1 H), 4.65 (dd,
J = 9.0, 9.1 Hz, 1 H), 5.52 (dd, J = 8.8, 3.5 Hz, 1 H), 6.52 (d, J = 9.2
Hz, 1 H), 6.82 (d, J = 7.2 Hz, 2 H), 7.06 (dd, J = 7.7, 7.6 Hz, 2 H),
7.27–7.48 (m, 15 H).
(2R,3S)-3-Hydroxy-3-phenyl-2-phenylselanyl-1-[(4R)-4-phe-
nyl-2-thioxothiazolidin-3-yl]propan-1-one (7a)
[a]D24 –411 (c 0.335, CHCl3).
IR (KBr): 3520, 3030, 1680, 1335, 1300, 1240, 1150, 1040, 735,
700 cm–1.
13C NMR (75 MHz, CDCl3): d = 184.4, 168.2, 139.6, 138.2, 137.3,
129.3, 129.2, 129.1, 128.9, 128.4, 128.2, 127.7, 126.9, 123.5, 73.5,
70.7, 61.7, 49.9.
1H NMR (300 MHz, CDCl3): d = 2.94 (dd, J = 11.1, 1.5 Hz, 1 H),
3.03 (br s, 1 H, OH), 3.63 (dd, J = 11.1, 8.4 Hz, 1 H), 4.58 (dd,
J = 9.1, 1.7 Hz, 1 H), 5.98 (dd, J = 8.5, 1.7 Hz, 1 H), 6.27 (d, J = 9.1
Hz, 1 H), 7.09 (m, 4 H), 7.28–7.33 (m, 6 H), 7.44 (br s, 5 H).
Anal. Calcd for C24H21NO3SSe: C, 59.75; H, 4.39; N, 2.90; S, 6.65.
Found: C, 59.89; H, 4.27; N, 2.94; S, 6.62.
13C NMR (75 MHz, CDCl3): d = 201.3, 168.6, 139.7, 138.8, 137.1,
129.2, 129.0; 128.7, 128.4, 128.2, 127.5, 126.0, 124.3, 71.5, 69.6,
51.4, 35.5.
(2R,3S)-3-Hydroxy-3-(4-methoxyphenyl)-2-phenylselanyl-1-
[(4R)-4-phenyl-2-thioxooxazolidin-3-yl]propan-1-one (6b)
[a]D 24 –294 (c 0.465, CHCl3).
Anal. Calcd for C24H21NO2S2Se: C, 57.82; H, 4.25; N, 2.81; S,
12.86. Found: C, 57.68; H, 4.22; N, 2.82; S, 12.65.
IR (KBr): 3470, 2960, 1690, 1515, 1370, 1365, 1305, 1250, 1180,
1141, 745, 700 cm–1.
(2R,3S)-3-Hydroxy-3-(4-methoxyphenyl)-2-phenylselanyl-1-
[(4R)-4-phenyl-2-thioxothiazolidin-3-yl]propan-1-one (7b)
[a]D24 –421 (c 0.38, CHCl3).
1H NMR (300 MHz, CDCl3): d = 3.00 (br s, 1 H, OH), 3.80 (s, 3 H),
4.44 (dd, J = 9.2, 3.5 Hz, 1 H), 4.50 (d, J = 9.5 Hz, 1 H), 4.68 (t,
J = 9.0 Hz, 1 H), 5.54 (dd, J = 8.8, 3.5 Hz, 1 H), 6.52 (d, J = 9.5 Hz,
1 H), 6.83 (m, 4 H), 7.08 (dd, J = 7.6, 7.8 Hz, 2 H), 7.29 (m, 3 H),
7.41–7.50 (m, 5 H).
IR (KBr): 3445, 2960, 1685, 1512, 1305, 1250, 1150, 1030, 740,
695 cm–1.
1H NMR (300 MHz, CDCl3): d = 2.96 (d, J = 11.3 Hz, 1 H), 2.98 (br
s, 1 H, OH), 3.68 (dd, J = 11.3, 8.7 Hz, 1 H), 3.80 (s, 3 H), 4.53 (d,
J = 8.5 Hz, 1 H), 6.02 (d, J = 8.2 Hz, 1 H), 6.27 (d, J = 9.2 Hz, 1 H),
6.84 (d, J = 8.7 Hz, 2 H), 7.09 (m, 4 H), 7.28 (m, 3 H), 7.45 (br s, 5
H).
13C NMR (75 MHz, CDCl3): d = 184.4, 168.1, 159.4, 138.3, 137.4,
131.7, 129.3, 129.2, 129.1, 128.9, 126.9, 123.4, 113.8, 73.4, 70.2,
61.7, 55.2, 49.8.
Anal. Calcd for C25H23NO4SSe: C, 58.59; H, 4.52; N, 2.73; S, 6.26.
Found: C, 58.72; H, 4.51; N, 2.78; S, 6.24.
13C NMR (75 MHz, CDCl3): d = 201.2, 168.4, 159.4, 138.9, 137.1,
131.7, 129.2, 128.9 (2 C), 128.7, 128.6, 126.0, 124.2, 113.7, 70.9,
69.6, 55.2, 51.3, 35.4.
(2R,3S)-3-Hydroxy-2-phenylselanyl-1-[(4R)-4-phenyl-2-
thioxooxazolidin-3-yl]hexan-1-one (6c)
[a]D 24 –258 (c 0.61, CHCl3).
Anal. Calcd for C25H23NO3S2Se: C, 56.80; H, 4.39; N, 2.65; S,
12.13. Found: C, 56.87; H, 4.44; N, 2.60; S, 11.81.
IR (KBr): 3500, 2960, 1690, 1370, 1350, 1200, 1145, 1015, 760,
700 cm–1.
(2R,3S)-3-Hydroxy-2-phenylselanyl-1-[(4R)-4-phenyl-2-
thioxothiazolidin-3-yl]hexan-1-one (7c)
[a]D24 –386 (c 0.60, CHCl3).
1H NMR (300 MHz, CDCl3): d = 0.86 (t, J = 7.0 Hz, 3 H), 1.34–1.53
(m, 4 H), 2.71 (d, J = 1.8 Hz, 1 H, OH), 3.58 (m, 1 H), 4.51 (dd,
J = 9.2, 3.8 Hz, 1 H), 4.83 (dd, J = 9.1, 9.0 Hz, 1 H), 5.74 (dd,
J = 8.8, 4.0 Hz, 1 H), 6.05 (d, J = 8.2 Hz, 1 H), 6.84 (dd, J = 7.8, 1.1
Hz, 2 H), 7.04 (dd, J = 7.8, 7.6 Hz, 2 H), 7.25 (m, 1 H), 7.45 (m, 5
H).
IR (KBr): 3500, 2960, 1680, 1300, 1250, 1150, 1120, 740, 700
cm–1.
1H NMR (300 MHz, CDCl3): d = 0.85 (t, J = 6.9 Hz, 3 H), 1.25–1.56
(m, 4 H), 2.68 (d, J = 1.9 Hz, 1 H, OH), 3.10 (dd, J = 11.4, 2.4 Hz,
1 H), 3.60 (m, 1 H), 3.92 (dd, J = 11.4, 8.6 Hz, 1 H), 5.85 (d, J = 8.1
Hz, 1 H), 6.29 (dd, J = 8.5, 2.2 Hz, 1 H), 6.99 (dd, J = 8.3, 1.4 Hz,
2 H), 7.08 (dd, J = 7.8, 7.6 Hz, 2 H), 7.26 (m, 1 H), 7.42–7.51 (m, 5
H).
13C NMR (75 MHz, CDCl3): d = 184.5, 169.6, 138.0, 137.0, 129.2,
129.1 (2 C), 128.8, 127.0, 124.0, 73.5, 68.0, 62.0, 49.2, 36.0, 18.9,
14.0.
Anal. Calcd for C21H23NO3SSe: C, 56.25; H, 5.17; N, 3.12; S, 7.15.
Found: C, 56.26; H, 5.28; N, 3.11; S, 7.13.
13C NMR (75 MHz, CDCl3): d = 201.2, 169.5, 138.8, 136.8, 129.0,
128.9, 128.8, 128.7, 126.2, 124.6, 69.9, 68.3, 50.6, 36.1, 35.4, 18.9,
14.0.
(2R,3S,4E)-3-Hydroxy-2-phenylselanyl-1-[(4R)-4-phenyl-2-
thioxooxazolidin-3-yl]oct-4-ene-1-one (6d)
[a]D 24 –322 (c 0.62, CHCl3).
Anal. Calcd for C21H23NO2S2Se: C, 54.30; H, 4.99; N, 3.02; S,
13.81. Found: C, 54.21; H, 5.06; N, 2.79; S, 13.55.
IR (KBr): 3515, 2930, 1685, 1670, 1370, 1300, 1255, 1180, 1020,
940, 745, 700 cm–1.
Synthesis 2007, No. 5, 719–724 © Thieme Stuttgart · New York