Development of a New Heterocycle-Forming Reaction and Kinetic Resolution with N-Heterocyclic Carbenes by Yinli Wang

Author:Yinli Wang
Language: eng
Format: epub, pdf
ISBN: 9789811393983
Publisher: Springer Singapore

mp 125–128 °C.

Compound S35

To a solution of S1 (375 mg, 1.70 mmol), Et3N (0.47 mL, 3.4 mmol), and Me3N·HCl (0.16 g, 1.7 mmol) in anhydrous toluene (1.7 mL) cooled in an ice–water bath was added MsCl (0.20 mL, 2.5 mmol) dropwise over 1 min. After 30 min, the reaction was quenched by the addition of saturated aqueous NH4Cl, and the organic layer was separated. The aqueous layer was extracted 3 times with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (toluene/CHCl3 1:1) to give S35 (477 mg, 94%) as a brown oil.

1H NMR (500 MHz, CDCl3) δ7.29 (d, J = 8.0, 2H), 7.14 (d, J = 8.0, 2H), 4.28 (t, J = 6.5, 2H), 3.01 (s, 3H), 2.51 (t, J = 7.0, 2H), 2.33 (s, 3H), 1.91 (m, 2H), 1.72 (m, 2H) ppm.

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