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3.0 Hz, 1H), 5.82-5.80 (m, 1H), 5.22 (d, J = 15.6 Hz, 1H), 4.98 (d, J = 15.6 Hz, 1H), 4.22 (d, J =
13.6 Hz, 1H), 3.85 (d, J = 7.4 Hz, 1H), 3.57 (s, 3H), 3.39 (d, J = 13.6 Hz, 1H), 3.32 (dd, J = 10.5,
8.3 Hz, 1H), 3.19 (dd, J = 10.3, 8.3 Hz, 1H), 3.11 (s, 6H), 2.51 (dd, J = 15.0, 6.6 Hz, 1H), 2.34-
2.24 (m, 2H), 2.17 (d, J = 0.5 Hz, 1H); 13 C NMR (75 MHz, CDCl3): δ 172.2, 169.8, 164.3,
151.8, 149.3, 140.4, 137.7, 137.1, 131.0, 129.5, 128.4, 128.2, 126.8, 126.2, 122.5, 108.6, 106.2,
73.0, 56.4, 52.1, 51.9, 45.6, 42.7, 39.3, 37.6, 28.6, 13.4; IR (thin film): ν 2948, 1734, 1622, 1402
cm -1 ; ESI-HRMS calcd for C38H40N3O6 m/z [M+1] + 566.2655; found 566.2653.
BzN O
MeO 2C
H
2-Benzoyl-1-isobutyl-4-methyl-6-methylene-5-oxo-1,2,3,5,6,6a-
hexahydrocyclopenta[c]pyrrole-1-carboxylic acid methyl ester (322). [Rh(CO)2Cl]2 (3 mg, 7
µmol) was placed in an oven-dried test tube, the atmosphere was replaced with Ar and DCE (0.5
mL) was added. Then dppb (6.3 mg, 15 µmol) in DCE (0.5 mL) was added at rt via a syringe
followed by AgBF4 (163 µL of a 0.1 M solution in toluene, 16 µmol). After 1 min, allenyne 321
(25 mg, 74 µmol) in DCE (0.5 mL) was added. After 30 min, half of the reaction mixture (0.6
mL) was taken out via a syringe and filtered on a small plug of silica gel to give 322 (5 mg,
37%).
1 H NMR (300 MHz, CDCl3): δ 7.60-7.57 (m, 2H), 7.52-7.43 (m, 3H), 6.15 (d, J = 2.0 Hz, 1H),
5.50 (d, J = 1.4 Hz, 1H), 4.56 (dt, J = 14.9, 1.6 Hz, 1H), 4.33 (d, J = 14.9 Hz, 1H), 3.52 (s, 3H),
2.80 (dd, J = 15.1, 7.0 Hz, 1H), 2.14 (dd, J = 15.1, 4.7 Hz, 1H), 2.05-1.90 (m, 1H), 1.77 (t, J =
1.8 Hz, 3H), 1.13 (d, J = 6.7 Hz, 3H), 1.08 (d, J = 6.7 Hz, 3H); 13 C NMR (75 MHz, CDCl3): δ
195.6, 171.0, 170.7, 162.9, 140.5, 135.7, 135.0, 131.1, 128.6, 127.4, 117.8, 71.0, 52.1, 50.8, 50.4,
40.0, 25.4, 24.4, 23.8, 9.1; IR (thin film): ν 2951, 1735, 1703, 1689, 1643, 1378 cm -1 ; MS m/z
322
277