Isoindolinones as Michael Donors under Phase Transfer Catalysis: Enantioselective Synthesis of Phthalimidines Containing a Tetrasubstituted Carbon Stereocenter
Dipartimento di Chimica e Biologia, Università di Salerno, Via Giovanni Paolo II, 132, 84084-Fisciano, SA, Italy
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Academic Editor: Diego A. Alonso
Molecules 2015, 20(5), 8484-8498; https://doi.org/10.3390/molecules20058484
Received: 14 April 2015 / Revised: 4 May 2015 / Accepted: 6 May 2015 / Published: 12 May 2015
(This article belongs to the Special Issue Phase-Transfer Catalysis)
Readily available chiral ammonium salts derived from cinchona alkaloids have proven to be effective phase transfer catalysts in the asymmetric Michael reaction of 3-substituted isoindolinones. This protocol provides a convenient method for the construction of valuable asymmetric 3,3-disubstituted isoindolinones in high yields and moderate to good enantioselectivity. Diastereoselectivity was also investigated in the construction of contiguous tertiary and quaternary stereocenters. The use of acrolein as Michael acceptor led to an interesting tricyclic derivative, a pyrroloisoindolinone analogue, via a tandem conjugated addition/cyclization reaction.
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Keywords:
synthetic methods; asymmetric catalysis; nitrogen heterocycles; conjugate addition; chiral phase transfer catalysts
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MDPI and ACS Style
Scorzelli, F.; Di Mola, A.; Palombi, L.; Massa, A. Isoindolinones as Michael Donors under Phase Transfer Catalysis: Enantioselective Synthesis of Phthalimidines Containing a Tetrasubstituted Carbon Stereocenter. Molecules 2015, 20, 8484-8498.
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