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Correction published on 23 May 2023, see Molecules 2023, 28(11), 4272.
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Article

Chiral Phase Transfer Catalysis in the Asymmetric Synthesis of a 3,3-Disubstituted Isoindolinone and Determination of Its Absolute Configuration by VCD Spectroscopy

by
Guglielmo Monaco
1,*,
Maximilian Tiffner
2,
Antonia Di Mola
1,
Wouter Herrebout
3,
Mario Waser
2 and
Antonio Massa
1,*
1
Dipartimento di Chimica e Biologia, Università di Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano, SA, Italy
2
Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040 Linz, Austria
3
Department of Chemistry, University of Antwerp, B-2020 Antwerp, Belgium
*
Authors to whom correspondence should be addressed.
Molecules 2020, 25(10), 2272; https://doi.org/10.3390/molecules25102272
Submission received: 20 April 2020 / Revised: 6 May 2020 / Accepted: 8 May 2020 / Published: 12 May 2020 / Corrected: 23 May 2023
(This article belongs to the Special Issue 25th Anniversary of Molecules—Recent Advances in Organic Synthesis)
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Abstract

In this work we report our endeavors toward the development of an asymmetric synthesis of a 3,3-disubstituted isoindolinone, dimethyl 2-(1-methyl-3-oxoisoindolin-1-yl)malonate, via asymmetric cascade reaction of 2-acetylbenzonitrile with dimethylmalonate and the determination of its absolute configuration (AC) by vibrational circular dichroism (VCD). Bifunctional ammonium salts, derived from trans-1,2-cyclohexanediamine in combination with inorganic bases under phase transfer conditions, were the most effective catalytic systems, leading to the target in high yields and moderate enantioselectivity. An efficient process of heterochiral crystallization allowed the increase of the enantiopurity up to 96% ee and in an acceptable overall yield. An important aim of the present work is the comparison of different VCD methodologies for AC determination of the target compound.
Keywords: organocatalysis; phase transfer catalysis; vibrational circular dichroism; heterocycles; isoindolinones organocatalysis; phase transfer catalysis; vibrational circular dichroism; heterocycles; isoindolinones
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MDPI and ACS Style

Monaco, G.; Tiffner, M.; Mola, A.D.; Herrebout, W.; Waser, M.; Massa, A. Chiral Phase Transfer Catalysis in the Asymmetric Synthesis of a 3,3-Disubstituted Isoindolinone and Determination of Its Absolute Configuration by VCD Spectroscopy. Molecules 2020, 25, 2272. https://doi.org/10.3390/molecules25102272

AMA Style

Monaco G, Tiffner M, Mola AD, Herrebout W, Waser M, Massa A. Chiral Phase Transfer Catalysis in the Asymmetric Synthesis of a 3,3-Disubstituted Isoindolinone and Determination of Its Absolute Configuration by VCD Spectroscopy. Molecules. 2020; 25(10):2272. https://doi.org/10.3390/molecules25102272

Chicago/Turabian Style

Monaco, Guglielmo, Maximilian Tiffner, Antonia Di Mola, Wouter Herrebout, Mario Waser, and Antonio Massa. 2020. "Chiral Phase Transfer Catalysis in the Asymmetric Synthesis of a 3,3-Disubstituted Isoindolinone and Determination of Its Absolute Configuration by VCD Spectroscopy" Molecules 25, no. 10: 2272. https://doi.org/10.3390/molecules25102272

APA Style

Monaco, G., Tiffner, M., Mola, A. D., Herrebout, W., Waser, M., & Massa, A. (2020). Chiral Phase Transfer Catalysis in the Asymmetric Synthesis of a 3,3-Disubstituted Isoindolinone and Determination of Its Absolute Configuration by VCD Spectroscopy. Molecules, 25(10), 2272. https://doi.org/10.3390/molecules25102272

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