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
4
Institute of Organic Chemistry
6
Altenbergerstr 69 4040 Linz Austria
|
Publication type: Journal Article
Publication date: 2017-02-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 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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38
Total citations:
38
Citations from 2025:
1
(2.63%)
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GOST
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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)
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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.
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 -
Cite this
BibTex (up to 50 authors)
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@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}
}
Cite this
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.