Tandem aza-Michael additions under high pressure: a shortcut to the azanorbornyl skeleton

Rulev A. Y., Yenil N., Pesquet A., Oulyadi H., Maddaluno J.

Tetrahedron, vol.62, no.23, pp.5411-5416, 2006 (SCI-Expanded, Scopus) identifier

  • Publication Type: Article / Article
  • Volume: 62 Issue: 23
  • Publication Date: 2006
  • Doi Number: 10.1016/j.tet.2006.03.070
  • Journal Name: Tetrahedron
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5411-5416
  • Manisa Celal Bayar University Affiliated: Yes

Abstract

The hyperbaric aza-Michael addition of mono- and diamines on α,β-unsaturated β,β-disubstituted mono- and diesters has been studied. While in the case of monoester, this reaction provides a β-aminoester presenting a quaternary center, a direct and efficient access to diester or lactams featuring an azanorbornyl skeleton was obtained when starting from a diester, following an unprecedented double aza-Michael addition. © 2006 Elsevier Ltd. All rights reserved.