Highly Enantioselective Synthesis of Halogenated Compounds Utilizing Lewis Acid or Organocatalyst

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  • Shibatomi Kazutaka
    Department of Environmental and Life Sciences, Toyohashi University of Technology

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  • ルイス酸触媒および有機分子触媒を活用した含ハロゲン化合物の高エナンチオ選択的合成法の開発
  • ルイスサン ショクバイ オヨビ ユウキ ブンシ ショクバイ オ カツヨウ シタ ガン ハロゲン カゴウブツ ノ コウエナンチオ センタクテキ ゴウセイホウ ノ カイハツ

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Abstract

Stereoselective incorporation of halogen atom(s) into organic molecules is a highly valuable process because chiral fluorinated compounds are recognized as fascinating building blocks of drug candidates and chiral chlorinated—, brominated—, iodinated compounds are useful synthetic intermediates for a range of optically active molecules. In this paper, we describe several synthetic methods for the construction of halogenated chiral carbon centers utilizing chiral Lewis acid catalysts or organocatalysts. For example, we succeeded in the enantioselective synthesis of α-chloro-α-fluoro carbonyl compounds, asymmetric chlorination of active methine compounds and their derivatization via SN2 substitution, and asymmetric Diels-Alder reaction of α-fluoroenones. Some methods for the asymmetric construction of trifluoromethylated chiral carbon centers are also described.

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