Publication:
Generation of ortho-quinone methides by p-TsOH on silica and their hetero-Diels-Alder reactions with styrenes

Issued Date

2009-05-15

Resource Type

Article

ISSN

00223263

DOI

10.1021/jo900504y

Other identifier(s)

2-s2.0-65949123776

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Journal of Organic Chemistry. Vol.74, No.10 (2009), 4009-4012

Suggested Citation

Paratchata Batsomboon, Wong Phakhodee, Somsak Ruchirawat, Poonsakdi Ploypradith Generation of ortho-quinone methides by p-TsOH on silica and their hetero-Diels-Alder reactions with styrenes. Journal of Organic Chemistry. Vol.74, No.10 (2009), 4009-4012. doi:10.1021/jo900504y Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/27421

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Title

Generation of ortho-quinone methides by p-TsOH on silica and their hetero-Diels-Alder reactions with styrenes

Author(s)

Paratchata Batsomboon
 Wong Phakhodee
 Somsak Ruchirawat
 Poonsakdi Ploypradith

Other Contributor(s)

Chulabhorn Graduate Institute
 Chulabhorn Research Institute
 The Institute of Science and Technology for Research and Development, Mahidol University

Abstract

(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.

Keyword(s)

Chemistry

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URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/27421

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