Chiral Brønsted Acid Catalyzed Stereoselective Addition of Azlactones to 3-Vinylindoles for Facile Access to Enantioenriched Tryptophan Derivatives

Authors


  • This work was supported by JSPS through a Grant-in-Aid for Scientific Research (Grant No. 20245021) and the Uehara Memorial Foundation. We gratefully acknowledge Prof. T. Iwamoto and Prof. S. Ishida (both from Tohoku University) for the X-ray crystal structure determination of 6. We also thank Prof. T. Ooi and Prof. D. Uraguchi (both from Nagoya University) and Dr. J. Takehara (Mitsubishi Chemical Group, Science and Technology Research Center, INC) for the HRMS analysis.

Abstract

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Syn-gled out: The syn diastereo- and enantioselective addition of azlactones to 3-vinylindoles was accomplished by using a chiral, binapthol-derived, Brønsted acid catalyst (see scheme). This method enables facile access to tryptophan derivatives with adjacent quaternary and tertiary stereogenic centers, which are potentially useful for the synthesis of peptidomimetics.

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