Allyl Cyanate-to-isocyanate Rearrangement for the Synthesis of Quaternary Stereocenter with Nitrogen Substituent

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Author(s)

Abstract

The stereochemistry and efficiency of an allyl cyanate-to-isocyanate rearrangement for the construction of quaternary stereocenter with nitrogen substituent was investigated by the synthesis of (<I>R</I>)-α-methylphenylalanine. The rearrangement was found to be stereospecific, and the chirality of allyl carbamate was transferred to that of the quaternary carbon bearing isocyanate group. These results establish that an allyl cyanate-to-isocyanate rearrangement is a useful method for the synthesis of natural products, that contain the quaternary carbon with nitrogen substituent.

Journal

  • Bioscience, Biotechnology, and Biochemistry

    Bioscience, Biotechnology, and Biochemistry 69(5), 939-943, 2005-05-23

    Japan Society for Bioscience, Biotechnology, and Agrochemistry

References:  10

Codes

  • NII Article ID (NAID)
    130000030324
  • NII NACSIS-CAT ID (NCID)
    AA10824164
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    09168451
  • NDL Article ID
    7322422
  • NDL Source Classification
    ZR7(科学技術--農林水産--農産) // ZR2(科学技術--生物学--生化学) // ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-G223
  • Data Source
    CJP  NDL  J-STAGE 
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