Sequential Rh(I)/Pd-catalyzed 1,4-addition/intramolecular allylation: stereocontrolled construction of gamma-butyrolactones and cyclopropanes.
The rhodium-catalyzed conjugate addition of functionalized vinyltin reagents to alkylidene Meldrum's acids, followed by Pd-catalyzed intramolecular allylation, is a direct entry into vinyl-substituted gamma-lactones via O-alkylation and vinylcyclopropanes via C-alkylation.
Fillion
Eric
E
Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1. efillion@uwaterloo.ca
Carret
Sébastien
S
Mercier
Lauren G
LG
Trépanier
Vincent E
VE
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D003521:Cyclopropanes; D007783:Lactones; D010165:Palladium; D012238:Rhodium; D015107:4-Butyrolactone