Institute of Crystallography - CNR

Highly chemoselective conjugate addition of lithium tetraorganozincates to coumarin derivatives and functionalization with electrophiles

DOI: https://doi.org/10.24820/ark.5550190.p011.877 Page 1 ©AUTHOR(S)
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Highly chemoselective conjugate addition of lithium tetraorganozincates to2
coumarin derivatives and functionalization with electrophiles3
4
Marzia Dell’Aera,a,b Filippo Maria Perna,b Paola Vitale,b Antonio Salomone,c5
Angela Altomare,a and Vito Capriati*b6
7 a Istituto di Cristallografia (IC-CNR), Via G. Amendola 122/o, 70125 Bari, Italy8
b Dipartimento di Farmacia-Scienze del Farmaco, Università degli Studi di Bari “Aldo Moro”, Consorzio9
C.I.N.M.P.I.S., Via E. Orabona 4, 70125, Bari, Italy10 c Dipartimento di Chimica, Università degli Studi di Bari “Aldo Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4,11
70125, Bari, Italy12
Email: vito.capriati@uniba.it13
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Dedicated to Professor Saverio Florio for his contribution to synthetic organic chemistry15
Received mm-dd-yyyy Accepted Manuscript mm-dd-yyyy Published on line mm-dd-yyyy16
Dates to be inserted by editorial office17
Abstract18
The nucleophilic addition (alkylation/arylation) of lithium tetraorganozincate species (R4ZnLi2) to coumarin19
derivatives takes place cleanly, with a short reaction time (30 min) and with high chemoselectivity, when20
working under mild conditions (0 °C) and with no additional solvents. Particularly remarkable is the21
diastereoselectivity of the reaction (up to 96:4), after trapping the resulting intermediates with external22
electrophiles. The stereochemistry of the major trisubstituted stereoisomer was assigned by combining 2D23
NOESY experiments with DFT calculations.

Year
2023
Journal
ARKIVOC (Online)
Impact factor
1.14
RESEARCH AREA
KEYWORDS
Authors
Dell'Aera, Marzia and Perna, Filippo Maria and Vitale, Paola and Salomone, Antonio and Altomare, Angela and Capriati, Vito
Authors IC CNR