A New Synthesis of 3‐Alkyl‐1‐isoindolinones.

Wang, Eng-Chi; Chen, Hsien-Fan; Feng, Pei-Kuan; Lin, Yu‐Li; Hsu, Ming-Kuan

doi:10.1002/chin.200307095

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“…General procedure for the synthesis of 3-substituted 3hydroxyisoindolinones via bromine-lithium exchange (13)(14)(15)(16)(17)(18)(19). Aryl bromide (4 equiv.)…”

Section: General Procedures For the Synthesis Of 3-substituted 3hydroxmentioning

confidence: 99%

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Synthesis of 3–aryl 3–hydroxyisoindolinones by the Addition of Grignard and Organolithium Reagents to Phthalimides

Glavač

Dokli

Gredičak

2017

COC

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Background: The 3-substituted 3-hydroxyisoindolinone motif is common to a variety of compounds with potent biological activities. In recent years, they have also been increasingly used as substrates in various asymmetric transformations. Current methods for their preparation either do not tolerate wide range of functional groups, or yield 3-hydroxyisoindolinones as N-substituted products, which makes them inapplicable as substrates for the asymmetric transformations.Objective: Aim of this study was a detailed examination of the synthesis of 3-substituted 3hydroxyisoindolinones comprising various functional groups and unsubstituted phthalimide nitrogen.Method: Grignard and organolithium reagents were employed as nucleophiles for the synthesis of 3substituted 3-hydroxyisoindolinones under various reaction conditions. Results: Phenyl substituents with electron donating groups are easily introduced by employing a Grignard reaction, while electron-poor arenes require a lithium exchange or direct lithiation strategy. The protocols are tolerant of various functional groups on the nucleophile, and a wide range of 3-hydroxyisoindolinones were afforded in good to excellent yields. Conclusion:Simple and inexpensive method for the synthesis of 3-substituted 3-hydroxyisoindolinone has been developed. By tweaking the reaction conditions, described protocols are tolerant of a wide range of functional groups, and yield 3-substituted isoindolinone alcohols with unsubstituted phthalimide nitrogen.

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“…General procedure for the synthesis of 3-substituted 3hydroxyisoindolinones via bromine-lithium exchange (13)(14)(15)(16)(17)(18)(19). Aryl bromide (4 equiv.)…”

Section: General Procedures For the Synthesis Of 3-substituted 3hydroxmentioning

confidence: 99%

“…3-Substituted 3-hydroxyisoindolinones are usually prepared by reacting phthalimide with the corresponding organometallic reagents [14][15][16][17]. Apart from Grignard and organolithium reagents, nickel-catalyzed additions of diethylzinc to phthalimides have also been developed [18][19][20].…”

Section: Introductionmentioning

confidence: 99%