Browsing by Author "Paratchata Batsomboon"

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    Generation of ortho-quinone methides by p-TsOH on silica and their hetero-Diels-Alder reactions with styrenes
    (2009-05-15) Paratchata Batsomboon; Wong Phakhodee; Somsak Ruchirawat; Poonsakdi Ploypradith; Chulabhorn Graduate Institute; Chulabhorn Research Institute; The Institute of Science and Technology for Research and Development, Mahidol University
    (Chemical Equation Presented) 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°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). © 2009 American Chemical Society.