Angewandte Chemie - International Edition p. 2134 - 2138 (2018)
Update date:2022-08-11
Topics:
Cheng, Qiang
Zhang, Fang
Cai, Yue
Guo, Yin-Long
You, Shu-Li
A stereodivergent synthesis of tetrahydrofuroindoles through palladium-catalyzed asymmetric dearomative formal [3+2] cycloaddition of nitroindoles with epoxybutenes was developed. The polarity of the solvent was found to play a key role in the diastereoselectivity. In toluene, good to excellent yields (70–99 %), diastereoselectivity (87/13->95/5 d.r.), and enantioselectivity (85/15–94/6 e.r.) were obtained, regardless of the properties of the substituents on nitroindoles. In acetonitrile, tetrahydrofuroindoles of a different diastereoisomer were produced with good to excellent yields (75–98 %) and stereoselectivity (78/22–93/7 d.r., 93/7–99/1 e.r.). Mechanistic studies were conducted to illustrate the origin of the diastereodivergency. The kinetic experiments indicate that the rate-determining step of this reaction is different in different solvents. ESI-MS experiments also support the existence of key palladium complex intermediates and the catalytic cycle of the reaction.
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