Sequential rhodium-catalyzed stereo- and regioselective addition of organoboron derivatives to the alkyl 4-hydroxy-2-alkynoates/lactonizaction reaction

Maria Alfonsi; Antonio Arcadi; Marco Chiarini; Fabio Marinelli

doi:10.1021/jo701629t

Sequential rhodium-catalyzed stereo- and regioselective addition of organoboron derivatives to the alkyl 4-hydroxy-2-alkynoates/lactonizaction reaction

J Org Chem. 2007 Dec 7;72(25):9510-7. doi: 10.1021/jo701629t. Epub 2007 Nov 6.

Authors

Maria Alfonsi¹, Antonio Arcadi, Marco Chiarini, Fabio Marinelli

Affiliation

¹ Department of Chemistry, Chemical Engineering and Materials, University of L'Aquila, via Vetoio-67010 Coppito (AQ), Italy.

PMID: 17983242
DOI: 10.1021/jo701629t

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Boron Compounds / chemistry*
Catalysis
Ketones / chemical synthesis
Ketones / chemistry
Lactones / chemical synthesis*
Lactones / chemistry
Molecular Structure
Rhodium / chemistry*
Stereoisomerism

Substances

Alkynes
Boron Compounds
Ketones
Lactones
Rhodium