A [3+3] cyclization strategy for asymmetric synthesis of alkyl substituted piperidine-2-ones using 1,2-cyclic sulfamidates: A formal synthesis of (S)-coniine from l-norvaline

Karanfil A., Balta B., ESKİCİ M.

Tetrahedron, vol.68, no.49, pp.10218-10229, 2012 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 68 Issue: 49
  • Publication Date: 2012
  • Doi Number: 10.1016/j.tet.2012.09.081
  • Journal Name: Tetrahedron
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.10218-10229
  • Keywords: Cyclic sulfamidates, Lithium triethylorthopropiolate, Cyclization, Piperidines
  • Manisa Celal Bayar University Affiliated: Yes

Abstract

Regioselective ring-opening reactions of a set of representative 1,2-cyclic sulfamidates with lithium triethylorthopropiolate proceeded efficiently to deliver the corresponding δ-amino-α,β-unsaturated esters after acidic hydrolysis. Hydrogenation of the unsaturated esters and subsequent thermal cyclization afforded the related alkyl substituted piperidine-2-ones. This approach represents a novel [3+3] cyclization strategy for the asymmetric synthesis of alkyl substituted piperidin-2-ones. Efficiency of the cyclization process is illustrated by a formal asymmetric synthesis of (S)-coniine from l-norvaline. © 2012 Elsevier Ltd. All rights reserved.