DOI: 10.1055/s-00000083

Synlett

References

Ligands L3b, L4a, L4b, L5, L6a and L6b were synthesized analogously to procedures described for related compounds, see: Şeker S, Barış D, Arslan N, Turgut Y, Pirinççioğlu N, Toğrul M.
Tetrahedron: Asymmetry 2014;
25: 411 ; To a solution of the corresponding amino alcohol (2 mmol) in MeOH (4 mL) was added a solution dimethyl oxalate (1 mmol) in MeOH (2 mL) dropwise at room temperature. The resulting mixture was stirred for 30 min. Within this time, a cloudy white solid was formed. The solid was filtered off and washed with cold MeOH (2 × 2 mL) to give the analytically pure product.Analytical data found for L4b1H NMR (300 MHz, DMSO-d6): δ = 7.96 (d, J = 8.2 Hz, 2 H), 7.29–7.19 (m, 10 H), 5.07–4.98 (m, 2 H), 3.60 (d, J = 5.3 Hz, 4 H), 3.29 (s, 6 H).13C NMR (75 MHz, DMSO-d6): δ = 159.30, 138.50, 128.66, 127.88, 126.86, 74.79, 59.12, 53.50.MS (ESI-TOF): m/z calcd 357.1814 [M+H]+, 379.1627 [M+Na]+; found: 357.1804 [M+H]+, 379.1627 [M+Na]+.L51H NMR (300 MHz, DMSO-d6): δ = 9.07 (d, J = 9.0 Hz, 2 H), 7.41–7.10 (m, 10 H), 4.79–4.56 (m, 2 H), 2.03–1.60 (m, 4 H), 0.82 (t, J = 7.3 Hz, 6 H).13C NMR (75 MHz, DMSO-d6): δ = 159.69, 142.88, 128.20, 126.89, 126.73, 54.99, 28.22, 11.20.MS (ESI-TOF): m/z calcd 347.1730 [M+Na]+; found: 347.1727 [M+Na]+.L6a1H NMR (300 MHz, DMSO-d6): δ = 8.86 (d, 2 H), 7.38–7.03 (m, 20 H), 5.06–4.91 (m, 2 H), 4.91–4.81 (m, 2 H).13C NMR (75 MHz, DMSO-d6): δ = 159.74, 140.25, 128.16, 127.05, 127.01, 63.95, 55.74.MS (ESI-TOF): m/z calcd 503.1941 [M+Na]+; found: 503.1945 [M+Na]+.L6b1H NMR (300 MHz, DMSO-d6): δ = 8.90–8.68 (m, 2 H), 7.41–7.05 (m, 20 H), 5.03–4.74 (m, 4 H).13C NMR (75 MHz, DMSO-d6): δ = 158.99, 142.87, 140.13, 128.60, 128.05, 127.54, 127.36, 127.09, 74.10, 59.46, 74.10, 59.46.MS (ESI-TOF): m/z calcd 503.1941 [M+Na]+; found 503.1949 [M+Na]+

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