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A stereoselective approach to 6-alkylated piperidinone & 2-piperidine via three-component vinylogous Mannich reactions (VMR) and a concise synthesis of (S)-anabasine

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
52
Issue
14
Identifiers
DOI: 10.1016/j.tetlet.2011.01.090
Keywords
  • Piperidine
  • Piperidinone
  • Vinylogous Mannich Reaction
  • Asymmetric Synthesis
  • Anabasine

Abstract

Abstract A three-component diastereoselective vinylogous Mannich-type reaction (VMR) with the silyl ketene acetal (1) was developed. Adducts from the reactions provided valuable intermediates for construction of a variety of chiral 6-alkylated piperidinone and 2-piperidine compounds. The strategy was applied in a concise synthesis (S)-anabasine.

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