Calixpyrrole derivatives: "multi hydrogen bond" catalysts for gamma-butenolide synthesis.
Calix[4]pyrrole (1), calix[2]m-benzo[4]pyrrole (2), 10alpha,20beta- and 10alpha,20alpha- bis(4-nitrophenyl)-calix[4]pyrroles 3 and 4, respectively, were found to exhibit various organocatalytic activities in the diastereoselective vinylogous addition reaction of 2-trimethylsilyloxyfuran (TMSOF, 7) to aldehydes. The gamma-hydroxybutenolide products are obtained in fairly good yields and with moderate diastereoselectivity. The structures of the catalysts, as well as the reaction conditions, strongly influence the efficiency of the reaction.
Cafeo
Grazia
G
Department of Chemistry, University of Salerno, via Ponte don Melillo, 84084 Fisciano (SA), Italy.
De Rosa
Margherita
M
Kohnke
Franz H
FH
Soriente
Annunziata
A
Talotta
Carmen
C
Valenti
Luca
L
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000447:Aldehydes / Q000737:chemistry; D047250:Calixarenes / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000737:chemistry; D006860:Hydrogen Bonding; D011166:Porphyrins / Q000737:chemistry*
C454640:2-trimethylsilyloxyfuran; D000447:Aldehydes; D005663:Furans; D011166:Porphyrins; C469811:calix(4)pyrrole; D047250:Calixarenes; C004511:butenolide; D015107:4-Butyrolactone