Isoindolinones as Michael Donors under Phase Transfer Catalysis: Enantioselective Synthesis of Phthalimidines Containing a Tetrasubstituted Carbon Stereocenter

Molecules

Francesco Scorzelli²  Antonia Di Mola²  Laura Palombi²  Antonio Massa¹ 

[1] Dipartimento di Chimica e Biologia, Università di Salerno, Via Giovanni Paolo II, 132, 84084-Fisciano, SA, Italy;

关键词: synthetic methods;    asymmetric catalysis;    nitrogen heterocycles;    conjugate addition;    chiral phase transfer catalysts;   

DOI  :  10.3390/molecules20058484

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.