1,2-Carbamoyl Migration on Enantio-enriched <i>α</i>-Lithioalkyl Carbamates Generated with <i>s</i>-Butyllithium/Sparteine: Steric Course and Mechanism

  • Katsuhiko Tomooka
    Department of Chemical Technology, Tokyo Institute of TechnologyMeguro-ku, Tokyo
  • Hideo Shimizu
    Department of Chemical Technology, Tokyo Institute of TechnologyMeguro-ku, Tokyo
  • Tadashi Inoue
    Department of Chemical Technology, Tokyo Institute of TechnologyMeguro-ku, Tokyo
  • Hikaru Shibata
    Department of Chemical Technology, Tokyo Institute of TechnologyMeguro-ku, Tokyo
  • Takeshi Nakai
    Department of Chemical Technology, Tokyo Institute of TechnologyMeguro-ku, Tokyo

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<jats:title>Abstract</jats:title> <jats:p>Alkyl N,N-diisopropylcarbamates, when lithiated with s-BuLi/(−)-sparteine in ether at −78 °C followed by warming to room temperature, are shown to undergo the 1,2-carbamoyl migration to give the α-hydroxy amides in &gt;95% ee with complete retention of configuration at the Li-bearing carbanion terminus. An addition-elimination mechanism is proposed.</jats:p>

収録刊行物

  • Chemistry Letters

    Chemistry Letters 28 (8), 759-760, 1999-08-01

    Oxford University Press (OUP)

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