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Synlett 2000; 2000(9): 1321-1323
DOI: 10.1055/s-2000-7155
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Enolates of Thiabicyclic Ketones as Stepping Stones Towards Synthesis of Sulfur Analogs of Tropane Alkaloids

Marek Majewski* , Marc DeCaire, Pawel Nowak, Fan Wang
  • *Department of Chemistry, University of Saskatchewan, 110 Science Pl., Saskatoon, SK, S7N 5C9, Canada; E-mail: majewski@sask.usask.ca
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Publication Date:
31 December 2000 (online)

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Enantioselective deprotonation of the bicyclic, sulfur bridged ketone TBON (8-thiabicyclo[3.2.1]octan-3-one, 1) with chiral lithium amides is described. Enolization proceeds with high levels of selectivity with some bases (most notably with lithium (S)-N-diphenylmethyl-1-phenylethanamide 3d) and the subsequent reaction of the resulting non-racemic lithium enolate with acyl cyanides allows efficient synthesis of sulfur analogs of tropane alkaloids (e. g., compound 8).

enolates - enantioselective deprotonation - bicyclic ketones