A new SmI2-mediated coupling reaction between N-acyl lactams and ketones or aldehydes is reported. The ring opening of these imides with samarium diiodide gives acyl samarium species, which are trapped by ketones or aldehydes to yield amido alpha-ketols. With an excess of SmI2, in the presence of ethanol, the end products are amidoketones. (C) 2000 Elsevier Science Ltd. All rights reserved.
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Sci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Toyko 1628601, JapanSci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Toyko 1628601, Japan
Mukaiyama, T
Arai, H
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Sci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Toyko 1628601, JapanSci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Toyko 1628601, Japan
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Korea Res Inst Chem Technol KRICT, Infect Dis Therapeut Res Ctr, Daejeon 34114, South Korea
Sungkyunkwan Univ, Dept Chem, Suwon 16419, South KoreaKorea Res Inst Chem Technol KRICT, Infect Dis Therapeut Res Ctr, Daejeon 34114, South Korea
Kwak, Dongmin
Jung, Sehwa
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Pohang Univ Sci & Technol POSTECH, Dept Chem, Pohang 37673, South KoreaKorea Res Inst Chem Technol KRICT, Infect Dis Therapeut Res Ctr, Daejeon 34114, South Korea
Jung, Sehwa
Ha, Hyeonbin
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Korea Res Inst Chem Technol KRICT, Infect Dis Therapeut Res Ctr, Daejeon 34114, South KoreaKorea Res Inst Chem Technol KRICT, Infect Dis Therapeut Res Ctr, Daejeon 34114, South Korea
Ha, Hyeonbin
Han, Taedong
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Dong A ST Res Inst, Discovery Chem, Yongin 17073, South KoreaKorea Res Inst Chem Technol KRICT, Infect Dis Therapeut Res Ctr, Daejeon 34114, South Korea
Han, Taedong
Ryu, Do Hyun
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Sungkyunkwan Univ, Dept Chem, Suwon 16419, South KoreaKorea Res Inst Chem Technol KRICT, Infect Dis Therapeut Res Ctr, Daejeon 34114, South Korea