SHORT PAPER
Stereoselective Transformation of Baylis-Hillman Adducts
219
Table 3 Data for Products 3a–ha
Product
Rfb
IR (Neat)
1H NMR (CDCl3/TMS, 200 MHz); d, J (Hz)
13C NMR (CDCl3/TMS, 50 MHz); d
n (cm–1)
3ac
0.57
1668, 1624
1688, 1621
1670, 1626
1668, 1622
1688, 1622
1670, 1622
1.26 (t, 3 H, J = 7.0), 2.47 (s, 3 H), 3.61 (q, 2 H,
J = 7.0), 4.27 (s, 2 H), 7.30−7.62 (m, 5 H), 7.72 (s,
1 H)
15.18, 26.09, 63.52, 66.03, 128.46,
129.32, 129.80, 134.82, 137.51,
143.74, 198.95
3b
3c
3d
3e
3f
0.60
0.51
0.62
0.58
0.51
1.25 (t, 3 H, J = 6.8), 2.39 (s, 3 H), 2.46 (s, 3 H),
3.58 (q, 2 H, J = 6.8), 4.28 (s, 2 H), 7.23 (d, 2 H,
J = 8.0), 7.46 (d, 2 H, J = 8.0), 7.69 (s, 1 H)
15.32, 21.43, 26.17, 63.64, 66.11,
129.37, 130.08, 132.11, 136.86,
139.86, 144.25, 199.16
1.24 (t, 3 H, J = 7.0), 2.46 (s, 3 H), 3.55 (q, 2 H,
J = 7.0), 4.23 (s, 2 H), 7.38 (d, 2 H, J = 8.4), 7.50
(d, 2 H, J = 8.4), 7.64 (s, 1 H)
15.15, 26.05, 63.44, 66.12, 128.75,
131.17, 133.40, 135.48, 138.12,
142.07, 198.61
1.28 (m, 9 H), 2.49 (s, 3 H), 2.97 (sept. 1 H,
J = 6.8), 3.63 (q, 2 H, J = 6.9), 4.32 (s, 2 H), 7.31
(d, 2 H, J = 8.2), 7.54 (d, 2 H, J = 8.2), 7.73 (s, 1 H)
15.24, 23.71, 26.04, 33.94, 63.51,
65.97, 126.63, 130.12, 132.33,
136.62, 144.27, 150.60, 199.01
1.22 (t, 3 H, J = 7.2), 2.48 (s, 3 H), 3.52 (q, 2 H,
J = 7.2), 4.17 (s, 2 H), 7.25−7.45 (m, 3 H), 7.60−
7.71 (m, 1 H), 7.83 (s, 1 H)
15.11, 26.18, 63.64, 66.10, 126.67,
129.35, 130.33, 130.92,133.29,
134.15, 138.73, 139.95, 198.61
1.23 (t, 3 H, J = 6.8), 2.47 (s, 3 H), 3.59 (q, 2 H,
J = 6.8), 3.86 (s, 3 H), 4.22 (s, 2 H), 6.88−7.09 (m,
2 H), 7.30−7.45 (m, 1 H), 7.64 (m, 1 H), 7.96 (s,
1 H)
15.21, 26.15, 55.43, 63.91, 66.01,
110.31, 120.44, 123.93, 130.73,
131.03, 137.11, 139.68, 157.69,
199.11
3g
3h
0.66
0.60
1672, 1620
1672, 1620
0.88 (t, 3 H, J = 6.8), 1.17 (t, 3 H, J = 7.0), 1.20−
1.55 (m, 10 H), 2.25–2.44 (m, 5 H), 3.47 (q, 2 H,
J = 7.0), 4.19 (s, 2 H), 6.81 (t, 1 H, J = 7.6)
13.98, 15.16, 22.56, 25.75, 28.81,
29.00, 29.33, 31.68, 62.78, 65.90,
138.23, 148.27, 198.69
0.97 (t, 3 H, J = 7.2), 1.19 (t, 3 H, J = 7.0), 1.51 (m,
2 H), 2.30−2.45 (m, 5 H), 3.49 (q, 2 H, J = 7.0),
4.21 (s, 2 H), 6.84 (t, 1 H, J = 7.6)
13.86, 15.19, 22.11, 25.80, 30.96,
62.83, 65.93, 138.46, 147.94, 198.71
a Satisfactory elemental analysis was obtained for 3a–g C 0.41%; H 0.48% and for 3h C +0.34%; H –0.56%).
b Eluent = 10% EtOAc in hexanes.
c MS (m/z): 204 (M+).
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Article Identifier:
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Synthesis 2000, No. 2, 217–219 ISSN 0039-7881 © Thieme Stuttgart · New York