Sequential One-Pot InBr3-Catalyzed 1,4- then 1,2-Nucleophilic Addition to Enones Academic Article uri icon

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abstract

  • Low sensitivity toward traces of moisture and high tolerance of different functional groups make indium tribromide suitable for carrying out multistep synthetic sequences. In particular, we have realized a 1,4-conjugated addition of indoles/thiols to alpha,beta-unsaturated ketones mediated by a catalytic amount (10 mol %) of InBr(3) obtaining the desired beta-substituted ketones in good yields. The Lewis acidity of indium salts was not affected by coordinating and acid nucleophiles; therefore, the subsequent catalytic 1,2-addition of Me(3)SiCN to carbonyl compounds can be performed in one pot. With the optimized atom-efficient protocol, several polyfunctionalized alpha-silyloxy cyanohydrins were synthesized in good to excellent yields (up to 97%) and a notable level of simple 1,3-diastereoselection (up to 84:16) was recorded in the case of 2-cyclohexen-1-one 2c.

authors

  • Bandini, Marco
  • Cozzi, Pier Giorgio
  • Giacomini, Mita
  • Melchiorre, Paolo
  • Selva, Simona
  • Umani-Ronchi, Achille

publication date

  • May 2002