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R. Ballini et al.
PAPER
Table 4 a-Alkylated g-Ketoesters 7 Prepared
Producta
Yield
78
IR (film)
1H NMR (CDCl3/TMS)
d, J (Hz)
13C NMR (CDCl3)
d
n (cm–1)
7a
1732
0.9 (t, 3H, J = 6.7 Hz), 1.2–1.7 (m, 6H), 2.11
(s, 3H), 2.4 (d, 1H, J = 12.9), 2.9 (d, 1H, J = 17.3),
2.81-2.9 (m, 1H), 3.65 (s, 3H)
13.9, 22.8, 28.7, 29.0, 30.1, 43.6,
45.1, 51.4, 174.2, 205.8
7b
75
1719
0.9 (d, 3H, J = 6.8), 0.95 (d, 3H, J = 6.9), 1.8–2.0
(m, 1H), 2.2 (s, 3H), 2.4 (d, 1H, J = 12.3 Hz),
2.7–2.8 (m, 1H), 2.9 (d, 1H, J = 17.1), 3.68
(s, 3H)
18.2, 20.2, 30.8, 30.9, 41.9, 46.9,
52.2, 175.1, 207.8
7c
7d
7e
73
99
99
1735
1732
1735
0.9 (t, 3H, J = 7.1), 1.2–1.6 (m, 4H), 2.15 (s, 3H),
2.45 (d, 1H, J = 12.3), 2.9 (d, 1H, J = 17.3),
2.8–2.9 (m, 1H), 3.69 (s, 3H)
14.1, 20.0, 28.2, 34.8, 43.4, 45.3,
50.9, 174.5, 204.3
1.5–1.8 (m, 11H), 2.15 (s, 3H), 2.5 (d, 1H,
J = 12.1), 2.9 (d, 1H, J = 17.3 Hz), 2.91–3.1
(m, 1H), 3.4 (s, 3H)
26.8, 27.3, 30.0, 31.7, 33.7, 37.3,
42.5, 44.8, 51.1, 176.9, 207.5
1.5–1.7 (m, 4H), 2.18 (s, 3H), 2.3 (t, 2H, J = 6.7),
2.5 (d, 1H, J = 12.4), 2.9 (d, 1H, J = 15.2),
2.8–2.91 (m, 1H), 3.6 (s, 3H), 3.7 (s, 3H)
22.1, 22.4, 28.8, 30.4, 41.9, 44.7,
51.4, 51.5, 172.4, 174.9, 205.1
7f
99
99
1718
1.3 (s, 3H), 2.15 (s, 3H), 2.5 (d, 1H, J = 12.3), 2.9
(d, 1H, J = 15.3), 3.68 (s, 3H), 3.85–4.0 (m, 4H)
24.0, 25.1, 28.8, 31.9, 38.5, 42.8,
44.7, 51.5, 64.5, 110.0, 174.9, 205.1
7g
3400, 1715
1.18 (d, 3H, J = 6.0), 1.3–1.7 (m, 6H), 2.18
(s, 3H), 2.55 (d, 1H, J = 12.3), 2.9 (d, 1H,
J = 17.1), 2.8–2.9 (m, 1H), 3.7–3.8 (m, 1H)
22.7, 23.5, 28.8, 30.3, 40.2, 42.8,
44.7, 51.5, 67.9, 174.9, 205.1
7h
7i
99
95
99
1717, 1603
1710
1.7–2.0 (m, 4H), 2.15 (s, 3H), 2.6 (d, 1H,
J = 12.5), 2.9 (d, 1H, J = 17.3), 2.9–3.1 (m, 1H),
3.7 (s, 3H), 7.1–7.3 (m, 5H)
28.8, 31.4, 34.2, 43.7, 44.9, 51.5,
125.7, 128.0, 129.1, 142.6, 174.8,
205.1
1.5–1.6 (m, 4H), 2.12 (s, 3H), 2.15 (s, 3H), 2.5
(t, 2H, J = 6.7), 2.6 (d, 1H, J = 12.6), 2.9 (d, 1H,
J = 15.3 Hz), 2.8–2.9 (m, 1H), 3.63 (s, 3H)
21.3, 28.9, 29.4, 30.0, 41.0, 44.3,
44.7, 51.5, 174.9, 205.1, 209.1
7j
1732
1.2–1.7 (m, 6H), 2.2 (s, 3H), 2.3 (t, 2H, J = 6.7),
2.5 (d, 1H, J = 12.5), 2.9 (d, 1H, J = 15.2),
2.8–2.9 (m, 1H), 3.69 (s, 3H), 3.71 (s, 3H)
22.9, 26.6, 28.5, 28.76, 29.8, 43.87,
44.7, 51.5, 175.0, 205.1, 207.7
a Satisfactory microanalyses obtained: C ± 0.15, H ± 0.14.
(b) Rosini, G.; Ballini, R. Synthesis 1988, 833.
References
(c) Ballini, R. In Studies in Natural Products Chemistry; Vol.
19; Atta-ur-Rahman Ed.; Elsevier: Amsterdam, 1997, p 117.
(9) (a) Ballini, R.; Petrini, M.; Marcantoni, E.; Rosini, G.
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(10) (a) Ballini, R.; Petrini, M. Synthesis 1986, 1024.
(b) Ballini, R.; Petrini, M.; Rosini, G. Synthesis 1987, 711.
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(4) Ellison, R. A. Synthesis 1973, 397.
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(6) Stetter, H.; Kuhlmann, H. Org. React. 1991, 40, 407.
(7) See for example:
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1990, 31, 5509.
Article Identifier:
1437-210X,E;1999,0,07,1236,1240,ftx,en;Z08598SS.pdf
(8) (a) Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia
1979, 33, 1.
Synthesis 1999, No. 7, 1236–1240 ISSN 0039-7881 © Thieme Stuttgart · New York