Reactions of zinc enolates derived from 1-aryl-2-bromo-alkanones and 1-aryl-2-bromo-2-phenylethanone with 3-aroyl-6-bromochromen-2-ones and 2-benzoylbenzo[f]chromen-3-one

Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives

“…Melting points were measured on a standard melting point apparatus and are uncorrected. 1 H NMR spectra were recorded on a 400 MHz spectrometer, while 13 C NMR spectra were recorded on a 100 MHz instrument. Chemical shifts are reported in δ ppm referenced to an internal TMS standard for 1 H NMR and chloroform-d (δ = 77.0 ppm) for 13 C NMR.…”

“…1 H NMR spectra were recorded on a 400 MHz spectrometer, while 13 C NMR spectra were recorded on a 100 MHz instrument. Chemical shifts are reported in δ ppm referenced to an internal TMS standard for 1 H NMR and chloroform-d (δ = 77.0 ppm) for 13 C NMR. HRMS spectra were recorded using FAB (TOF analyzer) or ESI (TOF analyzer).…”

“…6-Bromo-3-(4-bromobenzoyl)-2H-chromen-2-one (1ae). 13 Following the typical procedure TP-1, the desired product 1ae was obtained as a white solid (2962.9 mg, 73%). 5, 157.5, 153.2, 144.4, 135.8, 134.9, 131.7, 131.6, 131.4, 128.1, 126.8, 120.1, 118.5, 116. 8, 153.6, 143.6, 136.2, 136.1, 133.3, 132.3, 132.1, 131.3, 129.7, 129.1, 128.7, 128.4, 127.9, 127.0, 124.5, 119.7, 118.7, 117.6.…”

“…1 H NMR (400 MHz, CDCl 3 , 25 °C) δ/ppm 8.00 (s, 1H), 7.78 (d, J = 4.1 Hz, 1H), 7.77−7.68 (m, 3H), 7.31 (d, J = 9.7 Hz, 1H), 7.17 (s, 1H). 13 C NMR (100 MHz, CDCl 3 , 25 °C) δ/ppm 182. 4, 157.5, 153.4, 143.1, 142.6, 136.3, 136.0, 135.3, 131.2, 128.4, 127.9, 119.5, 118.7, 117.6.…”

“…1 H NMR (400 MHz, CDCl 3 , 25 °C) δ/ppm 8.42 (s, 1H), 7.43 (t, J = 7.8 Hz, 2H), 6.89 (d, J = 9.6 Hz, 1H), 4.88 (s, 1H), 4.30 (q, J = 7.2 Hz, 4H), 1.32 (t, J = 7.2 Hz, 6H). 13 C NMR (100 MHz, CDCl 3 , 25 °C) δ/ ppm 168. 5, 165.9, 160.0, 136.0, 134.2, 119.8, 119.3, 110.2, 72.4, 62.5, 13.9.…”