volume 73 issue 7 pages 819-828

A systematic study on the use of different organocatalytic activation modes for asymmetric conjugated addition reactions of isoindolinones

Francesco Scorzelli 1
Antonia Di Mola 2
Francesco De Piano 1
Consiglia Tedesco 1
Laura Palombi 1
Rosanna Filosa 3
Mario Waser 4, 5, 6
Antonio Massa 1
Publication typeJournal Article
Publication date2017-02-01
scimago Q3
wos Q2
SJR0.426
CiteScore4.1
Impact factor2.2
ISSN00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
In this article we describe a series of new asymmetric Michael reactions of carboxylate-3-substituted isoindolinones used as nucleophiles in the synthesis of valuable chiral tetrasubstituted derivatives. It has been shown that the reactivity and enantioselectivity strongly depend on the substitution pattern of the isoindolinone, requiring either cinchona-alkaloid based phase transfer catalysts or bifunctional tertiary amines organocatalysts. Moreover, prolinol-TMS ether-based secondary amine catalysts permitted the development of Michael/cyclization tandem reaction with cynnamaldehyde for the synthesis of aza-polycyclic derivatives.
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Scorzelli F. et al. A systematic study on the use of different organocatalytic activation modes for asymmetric conjugated addition reactions of isoindolinones // Tetrahedron. 2017. Vol. 73. No. 7. pp. 819-828.
GOST all authors (up to 50) Copy
Scorzelli F., Di Mola A., De Piano F., Tedesco C., Palombi L., Filosa R., Waser M., Massa A. A systematic study on the use of different organocatalytic activation modes for asymmetric conjugated addition reactions of isoindolinones // Tetrahedron. 2017. Vol. 73. No. 7. pp. 819-828.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.tet.2016.12.036
UR - https://linkinghub.elsevier.com/retrieve/pii/S0040402016313229
TI - A systematic study on the use of different organocatalytic activation modes for asymmetric conjugated addition reactions of isoindolinones
T2 - Tetrahedron
AU - Scorzelli, Francesco
AU - Di Mola, Antonia
AU - De Piano, Francesco
AU - Tedesco, Consiglia
AU - Palombi, Laura
AU - Filosa, Rosanna
AU - Waser, Mario
AU - Massa, Antonio
PY - 2017
DA - 2017/02/01
PB - Elsevier
SP - 819-828
IS - 7
VL - 73
SN - 0040-4020
SN - 1464-5416
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2017_Scorzelli,
author = {Francesco Scorzelli and Antonia Di Mola and Francesco De Piano and Consiglia Tedesco and Laura Palombi and Rosanna Filosa and Mario Waser and Antonio Massa},
title = {A systematic study on the use of different organocatalytic activation modes for asymmetric conjugated addition reactions of isoindolinones},
journal = {Tetrahedron},
year = {2017},
volume = {73},
publisher = {Elsevier},
month = {feb},
url = {https://linkinghub.elsevier.com/retrieve/pii/S0040402016313229},
number = {7},
pages = {819--828},
doi = {10.1016/j.tet.2016.12.036}
}
MLA
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MLA Copy
Scorzelli, Francesco, et al. “A systematic study on the use of different organocatalytic activation modes for asymmetric conjugated addition reactions of isoindolinones.” Tetrahedron, vol. 73, no. 7, Feb. 2017, pp. 819-828. https://linkinghub.elsevier.com/retrieve/pii/S0040402016313229.