Increasing the efficiency of the transannular Diels-Alder strategy via palladium(II)-catalyzed macrocyclizations.
Palladium(II)-catalyzed macrocyclizations of bis(vinylboronate ester) compounds are demonstrated to provide a strategically efficient approach to transannular Diels-Alder reaction substrates. In several systems reported, the macrocycle is preorganized such that cycloaddition at room temperature occurs concomitantly with cyclization. Numerous advantages over palladium(0)-catalyzed cross-coupling approaches are demonstrated.
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Robert G
RG
Iafe
Jonathan L
JL
Kuo
Dustin G
DG
Hochstatter
Tomomi
T
Saga
Jonathan W
JW
Turner
Craig A
CA
Merlic
D001896:Boron Compounds / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D001896:Boron Compounds; D006575:Heterocyclic Compounds, 3-Ring; D011083:Polycyclic Compounds; D010165:Palladium