51293-49-3Relevant academic research and scientific papers
Synthesis of 1,2-phenylenedimethanols by base-promoted reduction of isobenzofuran-1(3H)-ones with silane
Liu, Bin,Zhou, Xigeng
supporting information, p. 725 - 728 (2018/12/11)
An efficient method for preparation of substituted 1,2-phenylenedimethanols and aliphatic 1,4-diols that are valuable intermediates in organic synthesis, has been developed by the base-promoted reduction of isobenzofuran-1(3H)-ones and γ-lactones with silane under mild conditions. Compared with traditional procedures using stoichiometric amounts of metal hydrides and alkyl reductants, the present method avoids the use of sensitive reagents and is operationally simple and a broad variety of functional groups are tolerated.
Solid-phase synthesis of isoindolinones and naturally-occurring benzobutyrolactones (phthalides) using a cyclative-cleavage approach
Knepper, Kerstin,Ziegert, Robert E.,Br?se, Stefan
, p. 8591 - 8603 (2007/10/03)
Starting from Merrifield resin, 2-formylbenzoic acids were immobilized on solid supports. Reactions between immobilized 2-formylbenzoic acids and different organometallic reagents (Grignard reagents, zinc reagents, allyl silanes via Sakurai type reactions) furnished secondary alcohols which cyclized depending on the metal counter ion and reaction conditions, forming benzoannelated lactones. Asymmetric synthesis was possible on the resin using chiral [2.2]paracyclophane ligands. While the reaction of immobilized ortho-carboxy benzaldehydes with primary amines at elevated temperatures yielded 3-hydroxyisoindolinones, a reaction at ambient temperature allowed imine formation, which underwent 1,2-addition-cleavage reaction with various nucleophiles, yielding isoindolinones with three points of diversity.
