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Synlett 1999; 1999(9): 1468-1470
DOI: 10.1055/s-1999-2876
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Mn(III)/Cu(II)-Mediated Radical Cyclization of α-(Methylthio)acetamides

Hiroyuki Ishibashi* , Atsushi Toyao, Yoshifumi Takeda
  • *Faculty of Pharmaceutical Sciences, Kanazawa University, Takara-machi, Kanazawa 920-0934, Japan; Fax + 81(76)2 34-44 76; E-mail: isibasi@dbs.p.kanazawa-u.ac.jp
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Publication Date:
31 December 1999 (online)

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N-(Cyclohex-1-enyl)-α-(methylthio)acetamides 1, upon treatment with Mn(OAc)3 in the presence of Cu(OAc)2, underwent cyclization in a 5-endo-trig manner to give 1,4,5,6-tetrahydro-3-methylthio-2H-indol-2-ones 2. The radical mechanism has been proposed for the cyclization of 1.

radical cyclization - manganese(III) acetate - copper(II) acetate - carbamoylmethyl radical - neophyl rearrangement

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