G. R. Ganci, J. D. Chisholm / Tetrahedron Letters 48 (2007) 8266–8269
8269
the reaction was allowed to cool to room temperature,
taken up in ethyl ether, washed with 1 N NaOH (3·), dried
(MgSO4), and concentrated. Purification by silica gel
chromatography (60% CH2Cl2/hexanes) provided 111 mg
(64%) of alcohol 23 as a thick oil. Compound 23: TLC
Rf = 0.31 (60% CH2Cl2/hexanes); IR (film from CH2Cl2):
Acknowledgment
Acknowledgment is made to the Donors of the Ameri-
can Chemical Society Petroleum Research Fund for
the support of this research.
3501, 3027, 1726, 1495, 1244, 699 cmꢀ1
.
1H NMR
(300 MHz, CDCl3) d 7.63–7.67 (m, 2H), 7.16–7.41 (m,
8H), 4.15–4.29 (m, 2H), 3.93 (s, 1H), 2.75 (ddd, 1H,
J = 13.6, 11.8, 5.2 Hz), 2.62 (dt, 1H, J = 11.8, 4.9 Hz),
2.51 (ddd, 1H, J = 13.4, 11.6, 5.0 Hz), 2.34 (ddd, 1H,
J = 13.6, 11.8, 5.0 Hz), 1.27 (t, 1H, J = 7.5 Hz). 13C NMR
(75 MHz, CDCl3) d 175.6, 142.2, 142.1, 128.9, 128.8,
128.7, 128.1, 126.3, 125.9, 78.4, 63.0, 42.0, 30.6. HRMS
(ESI): m/z calcd for C18H20O3Na: 307.1304; found,
307.1304.
References and notes
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26. Characterization data for new compounds 21: TLC
Rf = 0.28 (30% Et2O/hexanes); IR (neat): 3505, 3061,
2937, 1727, 1602 cmꢀ1 1H NMR (300 MHz, CDCl3) d
.
7.10–7.63 (m, 10H), 4.22 (dt, 2H, J = 6.6, 1.8 Hz), 3.94 (s,
1H), 2.63 (t, 2H, J = 7.5 Hz), 2.00 (m, 2H), 1.88 (s, 3H).
13C NMR (75 MHz, CDCl3) d 176.1, 143.3, 141.2, 128.9,
128.8, 128.7, 128.3, 126.6, 125.7, 76.1, 65.9, 32.2, 30.5,
27.0. Anal. Calcd for C18H20O3: C, 76.03; H, 7.09. Found:
C, 76.16; H, 7.08. Compound 38: TLC Rf = 0.26
(CH2Cl2); IR (neat): 3453, 3019, 2981, 1714, 1682, 1427,
8. Oi, S.; Moro, M.; Fukuhara, H.; Kawanishi, T.; Inoue, Y.
Tetrahedron 2003, 59, 4351.
1
1358, 1272 cmꢀ1. H NMR (300 MHz, CDCl3) d 8.09 (t,
1H, J = 1.8 Hz), 7.91 (ddd, 1H, J = 7.8, 1.8, 1.2 Hz), 7.67
(ddd, 1H, J = 7.8, 1.8, 1.2 Hz), 7.49 (t, 1H, J = 7.8 Hz),
4.61 (s, 1H), 2.58 (s, 3H), 2.11 (s, 3H), 1.83 (s, 3H). 13C
NMR (75 MHz, CDCl3) d 209.5, 198.2, 142.7, 137.9,
131.2, 129.4, 128.6, 126.0, 80.2, 27.1, 24.7, 23.8. Anal.
Calcd for C12H14O3: C, 69.88; H, 6.84. Found: C, 70.28;
H, 6.65. Compound 44: TLC Rf = 0.29 (10% ethyl acetate/
hexanes); IR (neat): 3470, 2957, 2927, 2856, 1713,
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16. Recently Pd catalysts have been applied successfully to
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1
1456 cmꢀ1. H NMR (300 MHz, CDCl3) d 5.85 (td, 1H,
J = 15.3, 6.9 Hz), 5.51 (td, 1H, J = 15.3, 1.5 Hz), 4.01 (s,
1H), 2.22 (s, 3H), 2.02–2.21 (m, 2H), 1.46 (s, 3H), 1.23–
1.40 (m, 8H), 0.87 (t, 3H, J = 6.6 Hz). 13C NMR (75 MHz,
CDCl3) d 210.4, 133.5, 131.0, 79.1, 32.7, 32.0, 29.3, 29.2,
24.9, 24.0, 23.0, 14.4. HRMS (ESI): m/z calcd for
C12H22O2Na+ (M+Na+): 221.1512; found: 221.1508.
Compound 46: TLC Rf = 0.27 (10% ethyl acetate/hex-
anes); IR (neat): 3481, 2926, 2852, 1712, 1449, 1356 cmꢀ1
.
1H NMR (300 MHz, CDCl3) d 5.80 (dd, 1H, J = 15.6,
6.6 Hz), 5.46 (dd, 1H, J = 15.6, 1.2 Hz), 4.00 (s, 1H), 2.19
(s, 3H), 1.93–2.03 (m, 1H), 1.67–1.75 (m, 1H), 1.44 (s, 3H),
1.01–1.33 (m, 6H). 13C NMR (75 MHz, CDCl3) d 210.0,
138.5, 128.2, 78.7, 40.3, 32.6, 26.0, 25.9, 24.5, 23.5. HRMS
(ESI): m/z calcd for C12H20O2Na+ (M+Na+): 219.1355;
found, 219.1351.
27. Compounds 4,3 17,30 19,8 27,13 29,8 30,8 32,31 34,2 36,3
40,32 and 4233 have been previously reported.
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25. Representative experimental procedure: Ethyl 2-oxo-4-
phenyl butyrate 22 (130 mg, 0.611 mmol) was dissolved
in 1 mL of 9:1 1,2-dimethoxyethane/H2O which had been
degassed by bubbling argon through it for 20 min. This
solution was added to a flask containing dicarbonylaceto-
nato rhodium(I) (5.2 mg, 0.019 mmol, 3 mol %), dicyclo-
hexylphenyl phosphine 14 (10.8 mg, 0.037 mmol, 6 mol %)
and phenylboronic acid 1 (317 mg, 2.47 mmol) under
argon. The reaction was then heated to 80 ꢀC. After 24 h
32. Huang, Y. Monatsh. Chem. 2000, 131, 521.
33. Fronza, G.; Fuganti, C.; Pedrocchi-Fantoni, G.; Servi, S.
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