Tricarbonylchromium-Complexed Biaryls in Asymmetric Synthesis: Stereoselective Functionalization of Axially Chiral Biaryl Chromium Complexes

Yoshie Tanaka; Tomohiro Sakamoto; Ken Kamikawa; Motokazu Uemura

doi:10.1055/s-2003-37529

LETTER

Tricarbonylchromium-Complexed Biaryls in Asymmetric Synthesis: Stereoselective Functionalization of Axially Chiral Biaryl Chromium Complexes

Yoshie Tanaka^a,b, Tomohiro Sakamoto^a,b, Ken Kamikawa^a,b, Motokazu Uemura*^a,b
^a Department of Chemistry, Faculty of Integrated Arts and Sciences, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan
^b Research Institute for Advanced Sciences and Technology, Osaka Prefecture University, Sakai, Osaka 599-8570, Japan
Fax: +81(72)2549931; e-Mail: uemura@ms.cias.osakafu-u.ac.jp;

Abstract

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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

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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

Crystallographic 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, R_w = 0.095.