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DOI: 10.1055/s-2003-37529
Tricarbonylchromium-Complexed Biaryls in Asymmetric Synthesis: Stereoselective Functionalization of Axially Chiral Biaryl Chromium Complexes
Publication History
Publication Date:
26 February 2003 (online)
Abstract
An enantiomer of axially chiral syn-(biaryl)chromium with ortho-formyl group and both enantiomers of its anti-isomer were stereoselectively prepared from identical planar chiral arene chromium complex. The formyl group of the axially chiral chromium complexes was transformed by addition of MeLi, radical cyclization and β-lactam formation.
Key words
arene complexes - asymmetric synthesis - atropisomerism - biaryl - lactam
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References
Typical Procedure of Cycloaddition to Imine. To a solution of imine 19 (29 mg, 0.06 mmol) in dry CH2Cl2 (1.5 mL) was added PhOCH2COCl (0.025 mL, 0.18 mmol) and Et3N (0.05 mL, 0.36 mmol) at 0 °C under nitrogen, and stirred at 0 °C. The mixture was warmed to r.t. over 1 h, and quenched with sat. aq NaHCO3, extracted with Et2O. The organic layer was dried over MgSO4, and evaporated under reduced pressure. The residue was purified with silica gel chromatography to give cis-β-lactam 20 (26 mg, 70%). Mp 210-211 °C. 1H NMR (300 MHz, CDCl3): δ = 3.62 (3 H, s), 4.62 (1 H, d, J = 5.3 Hz), 5.13 (1 H, d, J = 5.3 Hz), 5.34 (1 H, d, J = 6.7 Hz), 5.44 (1 H, d, J = 6.7 Hz), 5.73 (1 H, t, J = 6.7 Hz), 6.79-6.85 (3 H, m), 7.00 (1 H, t, J = 7.6 Hz), 7.21-7.28 (4 H, m), 7.37-7.51 (5 H, m), 7.65 (1 H, t, J = 7.6 Hz), 7.81 (1 H, d, J = 7.6 Hz), 7.94 (1 H, d, J = 7.6 Hz), 8.00 (1 H, d, J = 7.6 Hz). IR (CHCl3): 1960, 1880, 1750, 1590 cm-1
11Crystallographic data for racemic 20 has been deposited with Cambridge Crystallographic Data Center. No. CCDC-1195543. Empirical formula: C35H25NO6Cr, M = 607.58, orthorhombic, space group, Pca21, a = 12.633, b = 10.3860, c = 21.752 Å, V = 2853.9(5) Å3, Z = 4, Dc = 1.414 g/cm3, F000 = 1256.00, MoKα (λ = 0.71075 Å), No of reflection measured 26037, reflection with I>3.00 σ (I), R = 0.049, Rw = 0.095.