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BzN
Bn
MeO2C 2-Benzoyl-1-benzyl-6-methylene-5-oxo-1,2,3,4,5,6-hexahydrocyclopenta[c]pyrrole-1-
290b
carboxylic acid methyl ester (290b). 1 H NMR (300 MHz, CDCl3): δ 7.46-7.35 (m, 5H), 7.27-
7.25 (m, 3H), 7.11-7.08 (m, 2H), 5.94 (s, 1H), 5.58 (s, 1H), 4.08 (d, J = 15.7 Hz, 1H), 4.04 (d, J
= 13.8 Hz, 1H), 3.84 (s, 3H), 3.56-3.52 (m, 2H), 2.85 (d, J = 22.5 Hz, 1H), 2.70 (d, J = 22.5 Hz,
1H); 13 C NMR (75 MHz, CDCl3): δ 201.5, 170.1, 169.2, 145.2, 142.5, 138.5, 136.2, 136.1,
130.1, 128.5, 127.9, 127.0, 126.4, 112.6, 74.3, 55.1, 52.9, 38.4, 36.2; IR (thin film): ν 2950,
1743, 1631, 1405, 1253 cm -1 ; ESI-HRMS calcd for C24H21NO4Na m/z [M+23] + 410.1368; found
410.1375.
Bz
O
N O
MeO 2C H
2-Benzoyl-1,4-dimethyl-6-methylene-5-oxo-1,2,3,5,6,6a-hexahydrocyclopenta[c]pyrrole-1-
carboxylic acid methyl ester (287c). Prepared by following general procedure O, using:
287c
74c (50 mg, 0.17 mmol), DMSO (120 µL, 1.68 mmol), Mo(CO)6 (55 mg, 0.21 mmol). Heated to
80 °C for 2 hours. The crude mixture (53 mg, >95%) was purified by flash chromatography
(gradient elution, hexanes-EtOAc, 9 : 1 to 2 : 1, v/v) to afford 287c (41 mg, 74 %). The correct
product ratios listed in Scheme 4.32 were determined in a separate experiment by integration of
the olefinic resonances in the 1 H NMR spectrum taken after complete removal of all volatiles
from a small reaction sample.
287c: (Rf = 0.23, TLC, hexanes-EtOAc, 2 : 1, v/v) 1 H NMR (300 MHz, CDCl3): δ 7.54-7.44 (m,
5H), 6.26 (d, J = 1.9 Hz, 1H), 5.44 (s, 1H), 4.58 (d, J = 15.7 Hz, 1H), 4.22 (d, J = 15.7 Hz, 1H),
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