Novel intermolecular and intramolecular generations of ortho-quinone methides and their formal [4+2]-cycloaddition reactions with olefins catalyzed by PtCl4 and AuCl3 under mild conditions have been developed. Good to excellent yields (up to 99%) and diastereoselectivity (up to >99:1) of the chromans were obtained. PtCl4 was found to be effective and compatible with various functional groups present in the substrates. A mechanism accounting for its catalytic cycle is proposed and discussed. © 2011 Elsevier Ltd. All rights reserved.
CITATION STYLE
Radomkit, S., Sarnpitak, P., Tummatorn, J., Batsomboon, P., Ruchirawat, S., & Ploypradith, P. (2011). Pt(IV)-catalyzed generation and [4+2]-cycloaddition reactions of o-quinone methides. Tetrahedron, 67(21), 3904–3914. https://doi.org/10.1016/j.tet.2011.03.059
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