LETTER
Synthesis of Novel Biaryl Analogues with a Fused Chiral Bicyclic Bridge
2419
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pressure, and the crude products were purified with column
chromatography on silica gel to afford 9b–d and 10b–d,
individually.
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Analytical Data of (2R)-9b
Mp 75–77 °C; [a]D23 –155.5 (c 1.0, CHCl3). 1H NMR (400
MHz, CDCl3): d = 7.89 (dd, J = 7.6, 1.2 Hz, 1 H), 7.72–7.82
(m, 2 H), 7.29–7.49 (m, 5 H), 6.33 (br, 1 H), 4.21 (br, 1 H),
1.82 (br, 3 H), 1.58 (br, 9 H). 13C NMR (100 MHz, CDCl3):
d = 169.1, 154.2, 133.5, 132.1, 130.7, 128.7, 128.7, 127.4,
126.4, 124.1, 123.6, 122.8, 81.6, 70.3, 55.0, 29.6, 28.3, 18.5,
16.9. ESI-HRMS: m/z calcd for C21H23N2O3 [M + H+]:
351.1700; found: 351.1703. HPLC: tR = 13.0 min [Chiralpak
OD-H (25 cm × 0.46 cm), Daicel Chemical Ind., Ltd.,
hexane–i-PrOH (50:1), 1.0 mL/min, >99% ee].
(22) C27H26N2O3, M = 426.52, orthorhombic, a = 9.920 (7),
b = 11.644 (3), c = 19.686 (6) Å, V = 2273.9 (18) Å3,
T = 293 K, space group P212121, Z = 4, 4035 reflections
measured, 3686 unique (Rint = 0.033) which were used in all
calculations. The final R1 = 0.0318 with wR2 = 0.0838. The
X-ray crystallographic data of compound (2S,12bS,M)-9d
was deposited at the Cambridge Crystallographic Data
Centre (CCDC-773497).
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Yan, H.; Zhong, R. G.; Hu, L. M. Synlett 2010, 2557.
(21) General Procedure for the Cyclisations of Compounds
8b–d
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2311.
To a well-stirred solution of compound 8b–d (1.0 equiv)in
anhyd acetonewas added TsOH (0.5 equiv) in one portion.
The resulting reaction solution wa s stir red at r.t. for 2–4 h.
The reaction solution was concentrated under reduced
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Synlett 2011, No. 16, 2415–2419 © Thieme Stuttgart · New York