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Sequential Rhodium-Catalyzed Stereo- and Regioselective Addition of Organoboron Derivatives to the Alkyl 4-Hydroxy-2-Alkynoates/Lactonizaction Reaction

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Maria Alfonsi,^† Antonio Arcadi,*^† Marco Chiarini,^‡ and Fabio Marinelli^†

Department of Chemistry, Chemical Engineering and Materials, University of L'Aquila, via Vetoio-67010 Coppito (AQ), Italy, and Department of Food Science, University of Teramo, Via Carlo R. Lerici, 1-64023 Mosciano Sant'Angelo (TE), Italy

J. Org. Chem., 2007, 72 (25), pp 9510–9517

DOI: 10.1021/jo701629t

Publication Date (Web): November 6, 2007

Section:

Heterocyclic Compounds (One Hetero Atom)

Abstract

The sequential rhodium-catalyzed addition/lactonization reaction of organoboron derivatives to alkyl 4-hydroxy-2-alkynoates would constitute a novel methodology for the synthesis of 4-aryl/heteroaryl/vinyl-2(5H)-furanones with an excellent control of the regio- and chemoselectivity. The role played by rhodium precatalyst, ligands, reaction medium, and the feature of organoboron derivatives has been explored.

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Synthesis of 4-Arylcoumarins via Cu-Catalyzed Hydroarylation with Arylboronic Acids
Yoshihiko Yamamoto and Naohiro Kirai
Organic Letters2008 10 (24), 5513-5516
- Synthesis of 4-Arylcoumarins via Cu-Catalyzed Hydroarylation with Arylboronic Acids
  Yoshihiko Yamamoto and Naohiro Kirai
  Organic Letters2008 10 (24), 5513-5516
  In the presence of 2−4 mol % of CuOAc, methyl phenylpropiolates having a MOM-protected hydroxy group at the ortho position underwent hydroarylation with various arylboronic acids in MeOH at ambient temperature, resulting in the formation of 4-...
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