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Synlett 1999; 1999(6): 719-720
DOI: 10.1055/s-1999-933097
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A Novel Enantioselective Synthesis of α-Azido Ketones

Dieter Enders* , Daniela Klein
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany; Fax + 49(241) 8888 127; E-mail: Enders@RWTH-Aachen.de
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Publikationsdatum:
07. Februar 2006 (online)

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The asymmetric synthesis of a range of α-azido ketones 5a-e is described. Key step of the procedure is the diastereo- and enantioselective nucleophilic substitution of an iodo group in α'-silylated α-iodo ketones 3a-e with NaN3 (de = 90-≥95%, ee ≥95%). Subsequent racemizationfree carbon-silicon bond cleavage using 3HF•Et3N gives the corresponding α-azido ketones 5a-e in good yield (54-86%) with high enantiomeric excesses (ee = 90-≥95%).

α-Azido Ketones - nucleophilic substitution - silyl ketones - asymmetric synthesis - SAMP-hydrazone