Nickel-Catalyzed [2+2+2] Cocyclization and Its Application to the Synthetic Organic Chemistry

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  • SATO Yoshihiro
    Graduate School of Pharmaceutical Sciences, Hokkaido University

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  • ニッケル触媒を用いた[2+2+2]環化反応の開発とその応用
  • ニッケル ショクバイ オ モチイタ 2 2 2 カンカ ハンノウ ノ カイハツ ト ソノ オウヨウ

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Abstract

A nickel (0)-catalyzed asymmetric [2+2+2] cocyclization has been realized for the first time. This reaction involves conceptually new enantiotopic group selective formation of a nickelacyclopentadiene intermediate and produces an isoindoline derivative (73% ee, 78% conv. yield) and an isoquinoline derivative (54% ee, 62% yield) having benzylic chiral carbon centers. The synthesizing methods of biaryls using the nickel-catalyzed [2+2+2] cocyclization were also developed. Two ways for the synthesis of biaryl using [2+2+2] cocyclization were investigated: one method is that biaryls synthesized from alkyne having a phenyl group and 2 equivalents of acetylene, and the other method is that those were synthesized from α,ω-diyne having a phenyl group at the α-position and acetylene.

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  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 121 (12), 961-969, 2001-12-01

    The Pharmaceutical Society of Japan

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