Synthesis of 5,5-disubstituted butenolides based on a Pd-catalyzed gamma-arylation strategy.
Methods for the construction of quaternary carbon centers are of great interest to synthetic chemists due to their presence in natural products. Development of the Pd-catalyzed arylation of butenolides with high selectivity for the gamma-position allows for a facile construction of quaternary centers. The preparation of a wide variety of gamma-aryl butenolides containing a number of functional groups is outlined. An application of this chemistry for a one-pot synthesis of a tricyclic tetrahydroisoquinolinone is demonstrated.
Hyde
Alan M
AM
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Buchwald
Stephen L
SL
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry
D044005:Tetrahydroisoquinolines; D010165:Palladium; C004511:butenolide; D015107:4-Butyrolactone