Download PDF
Synlett 1999; 1999(6): 719-720
DOI: 10.1055/s-1999-933097
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
07 February 2006 (online)

  PDF Download  Permissions and Reprints All articles of this category

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