Reductive Amination/Cyclization of ω-Trifluoromethyl Keto Esters to Trifluoromethylated δ-Amino Alcohols and Lactams

Authors

  • Wen Wan,

    1. Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, Republic of China, Fax: +86-21-66133380
    2. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China
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  • Jie Hou,

    1. Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, Republic of China, Fax: +86-21-66133380
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  • Haizhen Jiang,

    1. Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, Republic of China, Fax: +86-21-66133380
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  • Zongqian Yuan,

    1. Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, Republic of China, Fax: +86-21-66133380
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  • Goubin Ma,

    1. Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, Republic of China, Fax: +86-21-66133380
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  • Gang Zhao,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China
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  • Jian Hao

    1. Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, Republic of China, Fax: +86-21-66133380
    2. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China
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Abstract

A reductive amination/cyclization approach towards biologically interesting trifluoromethylated four- to seven-membered ring lactams from simply prepared ω-trifluoromethyl keto esters in good to excellent yields has been developed. In addition, trifluoromethylated δ-amino alcohols were also obtained directly from an unexpected reduction of the corresponding γ-imino esters in the presence of an excess amount of NaBH4.

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