A New Synthetic Approach to Efavirenz through Enantioselective Trifluoromethylation by Using the Ruppert–Prakash Reagent

Authors

  • Hiroyuki Kawai,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555, Japan, Fax: +81-52-735-7543
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  • Takashi Kitayama,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555, Japan, Fax: +81-52-735-7543
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  • Etsuko Tokunaga,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555, Japan, Fax: +81-52-735-7543
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  • Norio Shibata

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555, Japan, Fax: +81-52-735-7543
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Abstract

The organocatalyzed asymmetric synthesis of efavirenz was achieved in five steps from a commercially available substrate through the operationally simple, enantioselective trifluoromethylation of an alkynyl ketone by using the Ruppert–Prakash reagent. The present method provides the first example of the enantioselective synthesis of efavirenz by using a direct trifluoromethylation approach.

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