Generation of ortho-quinone methides by p-TsOH on silica and their hetero-Diels-Alder reactions with styrenes.
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).
Batsomboon
Paratchata
P
Program in Chemical Biology, Chulabhorn Graduate Institute, Vipavadee-Rangsit Highway, Bangkok, Thailand 10210.
Phakhodee
Wong
W
Ruchirawat
Somsak
S
Ploypradith
Poonsakdi
P
D002839:Chromans / Q000138:chemical synthesis / Q000737:chemistry; D045563:Indolequinones / Q000138:chemical synthesis* / Q000737:chemistry; D012822:Silicon Dioxide / Q000737:chemistry*; D020058:Styrene / Q000737:chemistry*; D014050:Toluene / Q000031:analogs & derivatives* / Q000737:chemistry
D002839:Chromans; D045563:Indolequinones; C068040:quinone methide; D014050:Toluene; D020058:Styrene; D012822:Silicon Dioxide; C065428:4-toluenesulfinic acid