4.7 Article

Generation of ortho-Quinone Methides by p-TsOH on Silica and Their Hetero-Diels-Alder Reactions with Styrenes

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 10, Pages 4009-4012

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo900504y

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Funding

  1. Thailand Research Fund [BRG5100813]

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2-Arylchromans were readily prepared from the hetero-Diels-Alder reactions of Styrenes with the ortho-quinone methides (o-QMs) which, in turn, were generated by treating the MOM-protected benzylacetate derivatives with p-TsOH immobilized on silica (PTS-Si) in toluene under mild conditions (0 degrees C to rt). The corresponding chromans were obtained in moderate to excellent yields (42-97%) and in moderate to excellent diastereoselectivity (up to > 99:1).

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