Sequential rhodium-catalyzed stereo- and regioselective addition of organoboron derivatives to the alkyl 4-hydroxy-2-alkynoates/lactonizaction reaction.
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.
Alfonsi
Maria
M
Department of Chemistry, Chemical Engineering and Materials, University of L'Aquila, via Vetoio-67010 Coppito (AQ), Italy.
Arcadi
Antonio
A
Chiarini
Marco
M
Marinelli
Fabio
F
D000480:Alkynes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D001896:Boron Compounds; D007659:Ketones; D007783:Lactones; D012238:Rhodium