Methyl (2S,5E)-6-(4-bromophenyl)-4-oxo-2-(tritylamino)hex-5-
enoate 11. Using the general procedure above gave 11 after 2 days
as a colourless solid (0.21 g, 96%). Mp 134–135 ◦C; nmax/cm-1
m/z (FAB) 502.2388 (MH+. C34H32NO3 requires 502.2382), 424
(45%), 258 (72), 243 (100), 166 (83), 158 (77).
Methyl (2S,5E)-6-(naphthalen-2-yl)-4-oxo-2-(tritylamino)hex-
5-enoate 15. Using the general procedure above gave 15 after
2 days as a yellow solid (0.16 g, 80%). Mp 62–63 ◦C; nmax/cm-1
=
(NaCl) 3021 (NH), 2950 (CH), 1737 (CO), 1659 (C C), 1608,
1488; [a]2D7 +64.6 (c 1.0, CHCl3); dH (400 MHz, CDCl3) 2.77 (1H,
dd, J 15.2, 7.0 Hz, 3-HH), 2.86–2.95 (2H, m, 3-HH and NH),
3.29 (3H, s, OMe), 3.75–3.83 (1H, m, 2-H), 6.66 (1H, d, J 16.2 Hz,
5-H), 7.14–7.21 (3H, m, ArH), 7.22–7.27 (7H, m, ArH and 6-H),
7.37–7.43 (2H, m, ArH), 7.46–7.57 (8H, m, ArH); dC (100 MHz,
CDCl3) 45.8 (CH2), 51.9 (CH3), 53.7 (CH), 71.2 (C), 124.9 (C),
126.2 (CH), 126.5 (CH), 127.9 (CH), 129.0 (CH), 129.7 (CH),
132.2 (CH), 133.3 (C), 141.7 (C), 145.7 (CH), 174.3 (C), 197.2 (C);
m/z (FAB) 554.1332 (MH+. C32H2979BrNO3 requires 554.1331),
478 (16%), 378 (3), 312 (13), 243 (100), 209 (16), 166 (43).
=
(NaCl) 3055 (NH), 2982 (CH), 1734 (CO), 1655 (C C), 1604,
1593, 1489, 1172; [a]D24 +64.1 (c 1.0, CHCl3); dH (400 MHz, CDCl3)
2.84 (1H, dd, J 15.1, 7.0 Hz, 3-HH), 2.92–3.00 (2H, m, 3-HH and
NH), 3.29 (3H, s, OMe), 3.79–3.86 (1H, m, 2-H), 6.80 (1H, d, J
16.2 Hz, 5-H), 7.15–7.30 (9H, m, ArH), 7.50–7.55 (8H, m, ArH),
7.62–7.69 (2H, m, 6-H and ArH), 7.84–7.89 (3H, m, ArH), 7.94
(1H, br s, ArH); dC (100 MHz, CDCl3) 45.9 (CH2), 52.1 (CH), 54.0
(CH3), 71.4 (C), 123.6 (CH), 126.6 (CH), 126.6 (CH), 126.9 (CH),
127.6 (CH), 128.0 (CH), 128.0 (CH), 128.2 (CH), 128.7 (CH),
128.9 (CH), 130.7 (CH), 132.0 (C), 133.4 (C), 134.5 (C), 143.5
(CH), 145.9 (C), 174.6 (C), 197.6 (C); m/z (FAB) 526.2388 (MH+.
C36H32NO3 requires 526.2382), 448 (7%), 273 (8), 243 (100), 181
(19), 165 (24).
Methyl (2S,5E)-6-(2-bromophenyl)-4-oxo-2-(tritylamino)hex-5-
enoate 12. Using the general procedure above gave 12 after 24 h
as a colourless oil (0.2 g, 78%). nmax/cm-1 (NaCl) 3021 (NH), 2950
(CH), 1737 (CO), 1437, 1204, 1027; [a]2D5 +48.6 (c 1.0, CHCl3); dH
(400 MHz, CDCl3) 2.82 (1H, dd, J 15.4, 6.8 Hz, 3-HH), 2.88–
2.97 (2H, m, NH and 3-HH), 3.30 (3H, s, OMe), 3.78–3.83 (1H,
m, 2-H), 6.60 (1H, d, J 16.2 Hz, 5-H), 7.13–7.33 (11H, m, ArH),
7.48–7.53 (6H, m, ArH), 7.59 (2H, td, J 8.0, 1.1 Hz, ArH), 7.85
(1H, d, J 16.2 Hz, 6-H); dC (100 MHz, CDCl3) 45.3 (CH2), 52.1
(CH), 53.8 (CH3), 71.3 (C), 125.9 (C), 126.6 (CH), 127.8 (CH),
127.9 (CH), 128.0 (CH), 128.9 (CH), 129.1 (CH), 131.6 (CH),
133.6 (CH), 134.4 (C), 141.7 (CH), 145.8 (C), 174.4 (C), 197.5 (C);
m/z (FAB) 554.1322 (MH+. C32H2979BrNO3 requires 554.1331),
478 (7%), 312 (13), 243 (100), 209 (7), 165 (19).
Methyl (2S,5E)-4-oxo-8-phenyl-2-(tritylamino)oct-5-enoate 16.
Using the general procedure above gave 16 after 2 days as a yellow
oil (0.15 g, 93%). nmax/cm-1 (NaCl) 3027 (NH), 2948 (CH), 1738
27
=
(CO), 1667 (C C), 1626, 1492, 1448, 1205; [a]D +26.6 (c 1.0,
CHCl3); dH (400 MHz, CDCl3) 2.50 (2H, q, J 7.1 Hz, 7-H2),
2.63 (1H, dd, J 15.3, 7.0 Hz, 3-HH), 2.70–2.80 (3H, m, 3-HH
and 8-H2), 2.85 (1H, br s, NH), 3.25 (3H, s, OMe), 3.67–3.74
(1H, m, 2-H), 6.06 (1H, d, J 15.9 Hz, 5-H), 6.76 (1H, dt, J 15.9,
7.1 Hz, 6-H), 7.12–7.30 (14H, m, ArH), 7.45–7.50 (6H, m, ArH);
dC (100 MHz, CDCl3) 32.4 (CH2), 32.6 (CH2), 43.2 (CH2), 50.1
(CH3), 51.9 (CH), 69.5 (C), 124.5 (CH), 125.0 (CH), 126.1 (CH),
126.6 (CH), 126.7 (CH), 127.0 (CH), 129.2 (CH), 138.9 (C), 144.0
(C), 145.3 (CH), 172.7 (C), 195.8 (C); m/z (FAB) 504.2534 (MH+.
C34H34NO3 requires 504.2539), 426 (69%), 252 (78), 243 (100), 166
(78), 160 (38).
Methyl (2S,5E)-6-(3-nitrophenyl)-4-oxo-2-(tritylamino)hex-5-
enoate 13. Using the general procedure above gave 13 after
5 days as a yellow oil (0.12 g, 56%). nmax/cm-1 (NaCl) 3022
(NH), 2951 (CH), 1737 (CO), 1613, 1530, 1352; [a]2D7 +49.3 (c 1.0,
CHCl3); dH (400 MHz, CDCl3) 2.79 (1H, dd, J 15.4, 7.0 Hz,
3-HH), 2.88–2.98 (2H, m, 3-HH and NH), 3.32 (3H, s, OMe),
3.77–3.85 (1H, m, 2-H), 6.79 (1H, d, J 16.2 Hz, 5-H), 7.16–7.21
(3H, m, ArH), 7.23–7.29 (6H, m, ArH), 7.46–7.52 (7H, m, ArH
and 6-H), 7.57 (1H, t, J 8.0 Hz, ArH), 7.81 (1H, d, J 8.0 Hz,
ArH), 8.24 (1H, d, J 8.0 Hz, ArH), 8.37 (1H, br s, ArH); dC
(100 MHz, CDCl3) 46.2 (CH2), 52.1 (CH3), 53.8 (CH), 71.3 (C),
122.6 (CH), 124.8 (CH), 126.9 (CH), 127.8 (CH), 128.6 (CH),
128.8 (CH), 130.1 (CH), 133.9 (CH), 136.2 (C), 140.1 (CH), 145.7
(C), 148.8 (C), 174.3 (C), 196.9 (C); m/z (FAB) 521.2074 (MH+.
C32H29N2O5 requires 521.2076), 443 (63%), 277 (31), 243 (100),
184 (44), 166 (79).
Methyl
(2S,5E,7E)-4-oxo-8-phenyl-2-(tritylamino)octa-5,7-
dienoate 17. Using the general procedure above gave 17 after
5 days as a yellow solid (0.08 g, 42%). Mp 66–67 ◦C; nmax/cm-1
(NaCl) 3024 (NH), 2950 (CH), 1737 (CO), 1619, 1586, 1448;
[a]2D7 +64.2 (c 1.0, CHCl3); dH (400 MHz, CDCl3) 2.72 (1H, dd,
J 15.0, 7.0 Hz, 3-HH), 2.83–2.93 (2H, m, 3-HH and NH), 3.26
(3H, s, OMe), 3.74–3.79 (1H, m, 2-H), 6.22 (1H, d, J 15.4 Hz,
7-H), 6.82–6.96 (1H, m, 5-H), 7.14–7.39 (13H, m, ArH and 6-H),
7.45–7.52 (9H, m, ArH and 8-H); dC (100 MHz, CDCl3) 45.6
(CH2), 52.0 (CH3), 53.9 (CH), 71.3 (C), 126.5 (CH), 126.7 (CH),
127.3 (CH), 127.9 (CH), 128.8 (CH), 128.9 (CH), 129.4 (CH),
129.8 (CH), 136.0 (C), 141.8 (CH), 143.5 (CH), 145.8 (C), 174.5
(C), 197.6 (C); m/z (FAB) 502.2387 (MH+. C34H32NO3 requires
502.2382), 424 (21%), 258 (22), 243 (100), 194 (17), 166 (91),
158 (55).
Methyl (2S,5E)-4-oxo-2-(tritylamino)-6-(3-vinylphenyl)hex-5-
enoate 14. Using the general procedure above gave 14 after
4 days as a yellow oil (0.12 g, 56%). nmax/cm-1 (NaCl) 3019 (NH),
=
2950 (CH), 1737 (CO), 1658 (C C), 1609, 1490, 1447, 1215, 1172;
[a]2D7 +52.0 (c 1.0, CHCl3); dH (400 MHz, CDCl3) 2.79 (1H, dd,
J 15.1, 7.0 Hz, 3-HH), 2.89–2.96 (2H, m, 3-HH and NH), 3.27
(3H, s, OMe), 3.76–3.85 (1H, m, 2-H), 5.31 (1H, d, J 10.9 Hz,
2¢-HH), 5.79 (1H, d, J 17.6 Hz, 2¢-HH), 6.66–6.76 (2H, m, 1¢-H
and 5-H), 7.13–7.28 (9H, m, ArH), 7.31–7.55 (11H, m, ArH and
6-H); dC (100 MHz, CDCl3) 45.8 (CH2), 52.0 (CH3), 53.9 (CH),
71.3 (C), 115.1 (CH2), 126.3 (CH), 126.7 (CH), 126.8 (CH), 127.8
(CH), 128.2 (CH), 128.4 (CH), 129.1 (CH), 129.2 (CH), 134.7 (C),
136.1 (CH), 138.4 (C), 143.2 (CH), 145.8 (C), 174.5 (C), 197.5 (C);
Methyl
(2S,5E)-6-(furan-2-yl)-4-oxo-2-(tritylamino)hex-5-
enoate 18. Using the general procedure above gave 18 after
4 days as a light brown solid (0.14 g, 81%). Mp 97–98 ◦C;
n
max/cm-1 (NaCl) 3058 (NH), 2951 (CH), 1737 (CO), 1607; [a]2D3
+42.9 (c 0.3, CHCl3); dH (400 MHz, CDCl3) 2.72 (1H, dd, J 15.1,
7.0 Hz, 3-HH), 2.82–2.94 (2H, m, 3-HH and NH), 3.27 (3H, s,
OMe), 3.74–3.81 (1H, m, 2-H), 6.47–6.50 (1H, m, 4¢-H), 6.59 (1H,
d, J 15.8 Hz, 5-H), 6.66 (1H, d, J 3.3 Hz, 3¢-H), 7.14–7.30 (11H,
m, 6-H, 5¢-H and ArH), 7.46–7.52 (6H, m, ArH); dC (100 MHz,
This journal is
The Royal Society of Chemistry 2009
Org. Biomol. Chem., 2009, 7, 4309–4316 | 4313
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