Literature DB >> 19385608

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

Paratchata Batsomboon1, Wong Phakhodee, Somsak Ruchirawat, Poonsakdi Ploypradith.   

Abstract

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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Year:  2009        PMID： 19385608     DOI： 10.1021/jo900504y

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

1.  An oxidation of benzyl methyl ethers with nbs that selectively affords either aromatic aldehydes or aromatic methyl esters.

Authors:  Abdelrahman S Mayhoub; Arindam Talukdar; Mark Cushman
Journal:  J Org Chem       Date:  2010-05-21       Impact factor: 4.354

Review 2.  Chemoenzymatic Total Synthesis of Natural Products.

Authors:  Suman Chakrabarty; Evan O Romero; Joshua B Pyser; Jessica A Yazarians; Alison R H Narayan
Journal:  Acc Chem Res       Date:  2021-02-18       Impact factor: 22.384

3.  Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols.

Authors:  Keith S Barbato; Yi Luan; Daniele Ramella; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2015-11-18       Impact factor: 6.005

4.  The domestication of ortho-quinone methides.

Authors:  Wen-Ju Bai; Jonathan G David; Zhen-Gao Feng; Marisa G Weaver; Kun-Liang Wu; Thomas R R Pettus
Journal:  Acc Chem Res       Date:  2014-12-03       Impact factor: 22.384
  4 in total

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