ZrCl4-catalyzed X-C/C-C bond formation for the geometric selective synthesis of (E)-β-iodo aza Morita-Baylis-Hillman (MBH) adducts

Qingjiang Li, Min Shi, Joshua M. Lyte, Guigen Li

Research output: Contribution to journalArticle

22 Scopus citations

Abstract

A geometric selective synthesis of (E)-β-iodo and β-alkyl vinyl ketones (MBH amino adducts) has been developed through a three-component Mannich-type reaction. The reaction was conveniently conducted by generating 3-iodo allenolate intermediates via the α,β-unsaturated addition of TMS-I to 3-butyn-2-one followed by a carbonyl addition onto N-aryl imines in the presence of ZrCl4 catalyst. The resulting β-iodo allylic amines can be readily converted into β-alkyl Morita-Baylis-Hillman adducts by performing Suzuki and Kumada cross-couplings.

Original languageEnglish
Pages (from-to)7699-7702
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number44
DOIs
StatePublished - Oct 30 2006

Keywords

  • Mannich-type reaction
  • Morita-Baylis-Hillman adduct
  • β-Iodovinyl ketone

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