Highly Diastereo- and Enantioselective Synthesis of α-Spiro-δ-lactams by an Organocascade Reaction

Kaiheng Zhang, Marta Meazza, Vojtěch Dočekal, Mark E. Light, Jan Veselý, Ramon Rios

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

An asymmetric synthesis of α-spiro-δ-lactams by an organocascade reaction of easily accessible starting materials has been accomplished. The catalytic sequence begins with enantioselective Michael addition of a β-ketoamide to an α,β-unsaturated aldehyde, catalyzed by a secondary amine catalyst, and is followed by hemiaminal annulation. Optically enantiopure compounds with three stereogenic centres are obtained in good yields and excellent selectivities (up to >20:1 dr and up to >99 % ee).

Original languageBritish English
Pages (from-to)1749-1756
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number13
DOIs
StatePublished - 3 Apr 2017

Keywords

  • Asymmetric synthesis
  • Enantioselectivity
  • Michael addition
  • Organocatalysis
  • Spirolactams

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