ORDER
REPRINTS
Synthesis of a-Amino Phosphonates
1681
1
20.29, 129.10, 129.46, 137.61, 146.25, 146.53, and 159.79; ESI-MS: m/z
þ
(
%): 350 (M þ 1, 18), 230 (08), 212 (40), 176 (12), 133 (58), 111 (12),
1
01 (100), and 79 (30). Anal. calcd for C H NO P: C, 61.88; H, 6.92; N,
18 24 4
4.01; P, 8.87. Found: C, 61.84; H, 6.94; N, 4.04; P, 8.85.
Compound (3a). Solid, m.p. 93–958C; IR (KBr) nmax: 3338, 2981, 2935,
862, 2362, 1661, 1600, 1498, 1451, 1313, 1225, 1160, 1027, 995, and
2
7
2
1 1
49 cm ; H NMR (CDCl 200 MHz, d): 1.25 (t, 6H, J ¼ 6.9 Hz), 1.46
3
,
(
(
m, 4H), 1.76 (m, 4H), 2.18 (m, 2H), 3.25, (bs, 1H), 4.02 (q, 4H), 6.80
t, 1H, J ¼ 7.8 Hz), 6.96 (d, 2H, J ¼ 7.8 Hz), and 7.12 (t, 2H, J ¼ 7.8 Hz);
3
1
13
P NMR (CDCl 400 MHz, d): 27.9; C NMR (CDCl 50 MHz, d):
3
,
3,
1
1
6.28, 16.39, 20.01, 20.24, 25.24, 30.19, 55.49, 58.66, 61.86, 62.01, 118.30,
þ
19.23, 128.52, and 145.25; ESI-MS: m/z (%): 312 (M þ 1, 26), 174
(
106), and 79 (38). Anal. calcd for C H NO P: C, 61.72; H, 8.42; N,
16 26 3
4
.50; P, 9.95. Found: C, 61.68; H, 8.43; N, 4.52; P, 9.94.
Compound (5a). Liquid; IR (KBr) nmax: 3320, 2930, 2880, 2800, 1640,
2
560, 1250, 1020, and 996 cm ; H NMR (CDCl , 200 MHz, d): 1.04,
1
1
1
3
(
t, 3H, J ¼ 6.8 Hz), 1.26 (t, 3H, J ¼ 6.8 Hz), 3.62 (s, OMe), 3.72 (m, 1H),
.90 (m, 1H), 4.08(m, 1H), 4.60 (d, 1H, J ¼ 25.5 Hz), 6.42 (d, 2H,
J ¼ 8.0 Hz), 6.62 (d, 2H, J ¼ 8.0 Hz), 7.01, (t, 2H, J ¼ 7.8 Hz), and 7.40
3
3
1
13
(
m, 2H); P NMR (CDCl , 400 MHz, d): 22.7; C NMR (CDCl , 50 MHz,
3 3
d): 16.21, 16.29, 16.41, 54.87, 55.60, 57.88, 63.23, 114.77, 115.24, 115.62,
1
1
15.67, 129.43, 129.54, 131.83, 140.27, 152.81, 154.93, 159.88, and
þ
64.85; ESI-MS: m/z (%): 368 (M þ 1, 100), 230 (80). Anal. calcd for
C H FNO P: C, 58.85; H, 6.31; F, 5.17; N, 3.81; P, 8.43. Found: C,
1
8
23
4
5
8.85; H, 6.28; F, 5.16; N, 3.83; P, 8.45.
Compound (7a). Liquid; IR (KBr) nmax: 3294, 2925, 2854, 1709, 1660,
598, 1562, 1493, 1463, 1306, 1235, 1093, 1024, 967, 818, and 757 cm
2
1
1 ;
H NMR (CDCl , 200 MHz, d): 1.24–1.32 (m, 6H), 4.23 (m, 4H), 4.40 (dd,
1
3
1
H, J ¼ 22.6 Hz, 2.1 Hz), 6.18–6.24 (m, 1H), 6.56–6.64 (m, 3H), 7.10
3
1
m, 2H), and 7.20–7.34 (m, 5H); P NMR (CDCl 400 MHz, d): 24.1;
13
(
NMR (CDCl , 50 MHz, d): 16.43, 29.67, 52.69, 55.75, 63.19, 114.94,
C
3,
3
1
23.11, 126.55, 127.94, 128.58, 129.10, 133.02, 133.32, and 145.27; ESI-
þ
MS: m/z (%): 380(M þ 1, 100), 354 (18), 279 (64), 25 (66), 242 (90), 216
(
32), 175 (46), 157 (48), and 125 (66). Anal. calcd for C H ClNO P: C,
19 23 3
6
9
0.08; H, 6.10; Cl, 9.33; N, 3.69; P, 8.15. Found: C, 60.12; H, 6.09; Cl,
.31; N, 3.70; P, 8.14.
Compound (11a). Liquid; IR (KBr) nmax: 3323, 2984, 2927, 2361, 1904,
760, 1612, 1569, 1512, 1455, 1317, 1304, 1241, 1164, 1096, 1027, 966, and
1
7
2
1 1
57 cm ; H NMR (CDCl , 200 MHz, d): 1.08 (t, 3H, J ¼ 7.0 Hz), 1.24
3
(
t, 3H, J ¼ 7.0 Hz), 1.96 (bs, 1H), 2.34 (s, 3H), 2.38 (s, 3H), 3.42 (d, 1H,
J ¼ 17.2 Hz), 3.70–4.10 (m, 6H), 7.08 (s, 4H), 7.12 (d, 2H, J ¼ 7.8 Hz),
3
1
and 7.24 (d, 2H, J ¼ 7.8 Hz); P NMR (CDCl , 400 MHz, d): 22.2;
3