Unprecedented Diastereoselective Arylogous Michael Addition of Unactivated Phthalides
Type
ArticleAuthors
Sicignano, MarinaSchettini, Rosaria
Sica, Luisa
Pierri, Giovanni
De Riccardis, Francesco
IZZO, Irene
Maity, Bholanath

Minenkov, Yury
Cavallo, Luigi

Della Sala, Giorgio
KAUST Department
Chemical ScienceChemical Science Program
KAUST Catalysis Center
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2019-04-08Online Publication Date
2019-04-08Print Publication Date
2019-05-23Embargo End Date
2020-04-08Permanent link to this record
http://hdl.handle.net/10754/656080
Metadata
Show full item recordAbstract
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.Citation
Sicignano, 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.201900168Sponsors
Financial 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-MSPublisher
WileyJournal
Chemistry – A European JournalAdditional Links
https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201900168Relations
Is Supplemented By:- [Dataset]
. DOI: 10.5517/ccdc.csd.cc20xzkh HANDLE: 10754/664724
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. DOI: 10.5517/ccdc.csd.cc20xzmk HANDLE: 10754/664725
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. DOI: 10.5517/ccdc.csd.cc20xzlj HANDLE: 10754/664726
ae974a485f413a2113503eed53cd6c53
10.1002/chem.201900168