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Synlett 1997; 1997(11): 1271-1272
DOI: 10.1055/s-1997-1013
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Asymmetric Synthesis of α'-Silylated α-Iodo Ketones via Iodination with Trifluoroiodomethane

Dieter Enders* , Daniela Klein, Gerhard Raabe, Jan Runsink
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany, Fax: (int.)+241 8888 127;E-mail: Enders@RWTH-Aachen.de
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Publication Date:
31 December 2000 (online)

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The diastereo- and enantioselective syntheses of various α'-t-butyldimethylsilyl-α-iodo ketones 4a-h is described. The carbon iodine bond formation is achieved using trifluoroiodomethane as the electrophilic iodination reagent. The iodo ketones 4 are obtained in good yields and with excellent diastereo- and enantiomeric excesses (de,ee ≥ 98%).

electrophilic iodination - α-iodo ketones - trifluoromethyl iodide - asymmetric synthesis - SMAP-hydrazone