Unprecedented Diastereoselective Arylogous Michael Addition of Unactivated Phthalides

Marina Sicignano, Rosaria Schettini, Luisa Sica, Giovanni Pierri, Francesco De Riccardis, Irene IZZO, Bholanath Maity, Yury Minenkov, Luigi Cavallo, Giorgio Della Sala

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

The first highly enantioselective arylogous Michael reaction (AMR) of 3-unsubstituted phthalides has been described. This phase-transfer methodology, which uses catalytic amounts of KOH/18-crown-6 catalyst in mesitylene in the presence of N,O-bis(trimethylsilyl)acetamide (BSA), gives access to a broad range of 3-monosubstituted phthalides with high levels of syn diastereoselectivity and good yields, starting from 3-unsubstituted derivatives and diverse α,β-unsaturated carbonyl compounds. The reaction also applies to unactivated 3-alkyl phthalides to afford 3,3-dialkyl derivatives. A plausible mechanism has been suggested. DFT analysis of possible transition states gives a rationale of the high syn diastereoselectivity observed and its correlation with the solvent's dielectric constant.
Original languageEnglish (US)
Pages (from-to)7131-7141
Number of pages11
JournalChemistry – A European Journal
Volume25
Issue number29
DOIs
StatePublished - Apr 8 2019

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