Synthesis of Optically Active Atropisomeric Anilide Derivatives and Their Application to Asymmetric Reaction.

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  • Kitagawa Osamu
    School of Pharmacy, Tokyo University of Pharmacy and Life Science
  • Taguchi Takeo
    School of Pharmacy, Tokyo University of Pharmacy and Life Science

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  • 光学活性アトロプ異性アニリド誘導体の合成と不斉反応への応用
  • コウガク カッセイ アトロプ イセイ アニリド ユウドウタイ ノ ゴウセイ ト フセイ ハンノウ エ ノ オウヨウ

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Abstract

N-Substituted anilide derivatives bearing a large substitutent such as a tent-Bu group at the ortho-position have atropisomerism due to the high rotation barrier of the N-Ar bond and resist racemization. We have succeeded in the synthesis of such atropisomeric N-Ar amides, imides and lactams with high optically purity and definite absolute configuration, and the development of various asymmetric reactions using them. Furthermore, catalytic asymmetric reaction with such atropisomeric anilide as a chiral ligand is also described.

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