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dc.contributor.authorSicignano, Marina
dc.contributor.authorSchettini, Rosaria
dc.contributor.authorSica, Luisa
dc.contributor.authorPierri, Giovanni
dc.contributor.authorDe Riccardis, Francesco
dc.contributor.authorIZZO, Irene
dc.contributor.authorMaity, Bholanath
dc.contributor.authorMinenkov, Yury
dc.contributor.authorCavallo, Luigi
dc.contributor.authorDella Sala, Giorgio
dc.date.accessioned2019-07-18T11:16:41Z
dc.date.available2019-07-18T11:16:41Z
dc.date.issued2019-04-08
dc.identifier.citationSicignano, M., Schettini, R., Sica, L., Pierri, G., De Riccardis, F., Izzo, I., … Della Sala, G. (2019). Unprecedented Diastereoselective Arylogous Michael Addition of Unactivated Phthalides. Chemistry – A European Journal, 25(29), 7131–7141. doi:10.1002/chem.201900168
dc.identifier.doi10.1002/chem.201900168
dc.identifier.urihttp://hdl.handle.net/10754/656080
dc.description.abstractThe 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.
dc.description.sponsorshipFinancial support was provided from the University of Salerno (FARB). The computing resources used within this project have been provided by CRESCO/ENEAGRID High Performance Computing infrastructure and its staff. We thank Dr Patrizia Iannece for HR-ESI-MS
dc.publisherWiley
dc.relation.urlhttps://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201900168
dc.rightsArchived with thanks to Chemistry – A European Journal
dc.subjectcrown compounds
dc.subjectdensity functional calculations
dc.subjectdiastereoselectivity
dc.subjectMichael addition
dc.subjectphthalides
dc.titleUnprecedented Diastereoselective Arylogous Michael Addition of Unactivated Phthalides
dc.typeArticle
dc.contributor.departmentChemical Science
dc.contributor.departmentChemical Science Program
dc.contributor.departmentKAUST Catalysis Center
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalChemistry – A European Journal
dc.rights.embargodate2020-04-08
dc.eprint.versionPost-print
dc.contributor.institutionDipartimento di Chimica e Biologia “Adolfo Zambelli”Università degli Studi di Salerno Via Giovanni Paolo II 132 84084 Fisciano SA Italy
dc.contributor.institutionMoscow Institute of Physics and Technology, MIPT Institutskiy Pereulok 9 141700 Dolgoprudny Moscow Region Russia
kaust.personMaity, Bholanath
kaust.personCavallo, Luigi
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc20xzkh
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc20xzmk
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc20xzlj
display.relations<b> Is Supplemented By:</b> <br/> <ul> <li><i>[Dataset]</i> <br/> . DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc20xzkh">10.5517/ccdc.csd.cc20xzkh</a> HANDLE: <a href="http://hdl.handle.net/10754/664724">10754/664724</a></li></ul><b> Is Supplemented By:</b> <br/> <ul> <li><i>[Dataset]</i> <br/> . DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc20xzmk">10.5517/ccdc.csd.cc20xzmk</a> HANDLE: <a href="http://hdl.handle.net/10754/664725">10754/664725</a></li></ul><b> Is Supplemented By:</b> <br/> <ul> <li><i>[Dataset]</i> <br/> . DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc20xzlj">10.5517/ccdc.csd.cc20xzlj</a> HANDLE: <a href="http://hdl.handle.net/10754/664726">10754/664726</a></li></ul>
dc.date.published-online2019-04-08
dc.date.published-print2019-05-23


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