Phosphine-catalyzed reactions of activated olefins tethered to cycloalkanones. substrate- and solvent-controlled synthesis of bicyclo[3.2.1]octanones, mixed acetals, and Morita-Baylis-Hillman products.
The n-Bu3P organocatalyzed reaction of cycloalkanones, i.e., cyclopentanones or 1,3-cyclopentanediones tethered to actived olefins, afforded selectively and in high yields three different types of products: bicyclo[3.2.1]octanones, mixed acetals, and Morita-Baylis-Hillman products. The progress of the reaction was closely related to the reaction medium and to the length of the tether located between the cyclopentanone (-dione) and the activated olefin.
Université de Strasbourg , Institut de Chimie, UMR Unistra-CNRS 7177, Laboratoire de Chimie Organique Synthétique, 1 rue Blaise Pascal, BP296/R8, 67008 Strasbourg, France.
Yanhui
Y
Wang
Alexis
A
Jaunet
Philippe
P
Geoffroy
Michel
M
Miesch
D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
D000080:Acetals; D000475:Alkenes; D001643:Bridged Bicyclo Compounds; D010720:Phosphines; D012997:Solvents; C044646:phosphine