Silver-catalyzed carbon dioxide incorporation and rearrangement on propargylic derivatives

Satoshi Kikuchi, Shunsuke Yoshida, Yuudai Sugawara, Wataru Yamada, Hau Man Cheng, Kohei Sekine, Izumi Iwakura, Taketo Ikeno, Tohru Yamada

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Abstract

A silver/DBU catalyst system was developed for the effective synthesis of cyclic carbonate and oxazolidinone from the reaction of CO2 with propargylic alcohols and propargylic amines, respectively, in high yields under mild conditions. It was found that the [3,3]-sigmatropic MeyerSchuster- type rearrangement of the propargylic alcohol was mediated by CO2 in DMF to afford the corresponding α,β-unsaturated carbonyl compounds in high yields. The silver salt combined with the chiral Schiff base ligand could be applied to enantioselective chemical CO2 incorporation into various bispropargylic alcohols to produce the corresponding cyclic carbonate in high yields with high enantioselectivity. The absolute configuration was determined by VCD spectroscopy as well as by X-ray analysis. These products were found to be active for the aminolysis reaction to afford the corresponding carbamate derivatives in high yields without any loss of optical purity.

Original languageEnglish
Pages (from-to)698-717
Number of pages20
JournalBulletin of the Chemical Society of Japan
Volume84
Issue number7
DOIs
Publication statusPublished - 2011 Jul 21

ASJC Scopus subject areas

  • Chemistry(all)

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    Kikuchi, S., Yoshida, S., Sugawara, Y., Yamada, W., Cheng, H. M., Sekine, K., Iwakura, I., Ikeno, T., & Yamada, T. (2011). Silver-catalyzed carbon dioxide incorporation and rearrangement on propargylic derivatives. Bulletin of the Chemical Society of Japan, 84(7), 698-717. https://doi.org/10.1246/bcsj.20110078