An article An Entry to Enantioenriched 3,3-Disubstituted Phthalides through Asymmetric Phase-Transfer-Catalyzed gamma-Alkylation Marina WOS:000538764000061 published article about MICHAEL ADDITION; CONVENIENT SYNTHESIS; METHYL ETHERS; CHEMISTRY; ACIDS; DIHYDRONAPHTHOQUINONES; CITALOPRAM; INHIBITORS; KETONES; CENTERS in [Sicignano, Marina; Schettini, Rosaria; Pierri, Giovanni; Marino, Maria Leda; Izzo, Irene; De Riccardis, Francesco; Della Sala, Giorgio] Univ Salerno, Dipartimento Chim & Biol Zambelli, I-84084 Fisciano, SA, Italy; [Bernardi, Luca] Alma Mater Studiorum Univ Bologna, Dept Ind Chem Toso Montanari, I-40136 Bologna, Italy; [Bernardi, Luca] Alma Mater Studiorum Univ Bologna, INSTM RU Bologna, I-40136 Bologna, Italy in 2020, Cited 63. COA of Formula: C8H6O2. The Name is Isobenzofuran-1(3H)-one. Through research, I have a further understanding and discovery of 87-41-2
A novel asymmetric phase-transfer-catalyzed gamma-alkylation of phthalide 3-carboxylic esters has been developed, giving access to 3,3-disubstituted phthalide derivatives, which present a chiral quaternary gamma-carbon in good to excellent yields and good enantioselectivities (74-88% ee). The enantiomeric purity could be substantially enhanced to 94-95% ee by recrystallization. Both electron-withdrawing and electron-releasing substituents are well tolerated on the phthalide core as well as on the aromatic moiety of the alkylating agent. This methodology, enabling the introduction of an unfunctionalized group at the phthalide gamma-position, fully complements previously reported organocatalytic strategies involving functionalized electrophiles, thus expanding the scope of accessible 3,3-disubstituted products. The high synthetic value of this asymmetric reaction has been proven by the formal synthesis of the naturally occurring alkaloid (+)-(9S,13R)-13-hydroxyisocyclocelabenzine.
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Reference:
Benzofuran – Wikipedia,
,Benzofuran | C8H6O – PubChem