Stereocontrolled synthesis of contiguous C(sp3)-C(aryl) bonds by lanthanide(III)-catalyzed domino aryl-Claisen [3,3]-sigmatropic rearrangements.
A domino [3,3]-sigmatropic aryl-Claisen rearrangement of cyclic and acyclic bisaryloxy-substituted alkenes can be performed in high yield by using Ln(fod)(3) catalysis to obtain bisphenolic products incorporating two contiguous aryl-C(sp(3)) bonds. Stereospecific rearrangement was observed for cyclic substrates. The precursor diaryl ethers were typically synthesized from the corresponding diols by double arylation procedures using either copper catalyzed coupling of aryltrifluoroborate salts or by S(N)Ar reaction.
Ramadhar
Timothy R
TR
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada, M5S 3H6.
Kawakami
Jun-ichi
J
Lough
Alan J
AJ
Batey
Robert A
RA
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003516:Cycloparaffins / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D028581:Lanthanoid Series Elements / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D003516:Cycloparaffins; D004987:Ethers; D028581:Lanthanoid Series Elements