Chiral bifunctional organocatalysts for enantioselective synthesis of 3-substituted isoindolinones

RSC Adv. 2023 Aug 15;13(35):24460-24465. doi: 10.1039/d3ra04350a. eCollection 2023 Aug 11.


A series of chiral bifunctional organocatalysts were prepared and used for enantioselective synthesis of 3-substituted isoindolinones from 2-formylarylnitriles and malonates through aldol-cyclization rearrangement tandem reaction in excellent yields and enantioselectivites (up to 87% yield and 95% ee) without recrystallization. In this investigation, we found that chiral tertiary-amine catalysts with a urea group can afford 3-substituted isoindolinones both in higher yields (87% vs. 77%) and enantioselectivities (95% ee vs. 46% ee) than chiral bifunctional phase-transfer catalysts.

PMID:37588978 | PMC:PMC10425721 | DOI:10.1039/d3ra04350a


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