Brønsted Acid Catalyzed Enantioselective α-Amidoalkylation in the Synthesis of Isoindoloisoquinolines

Aranzamendi, Eider; Sotomayor, Nuria; Lete, Esther

doi:10.1021/jo3000223

Cited by 66 publications

(34 citation statements)

References 43 publications

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“…In 2012, Lete's group explored another transformation by employing indoles as carbon nucleophiles . In this cyclization/alkylation sequence, chiral intermediate 15 could be trapped by indoles 16 to give the desired indolyl‐substituted phthalimidines 18 .…”

Section: Enantioselective Synthesis Of Isoindolinones By Using Organomentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Isoindolinones

Gao

Chen

Ding

et al. 2019

Chemistry An Asian Journal

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As important reactive species, isoindolinones represent a cluster of valuable building blocks for the construction of natural‐product‐like compounds. In particular, chiral isoindolinones are the key structural feature of naturally occurring bioactive molecules. During the past decade, great advances have been made in the asymmetric synthesis of isoindolinone skeleton compounds. Hence, recent progress in catalytic asymmetric synthesis of isoindolinones is reviewed here, with emphasis on chiral organocatalysis and transition metal complexes enabled transformations. Different organocatalysts (chiral phosphoric acids, phase transfer catalysts, chiral thioureas) and chiral transition‐metal complexes (Rh, Pd, Ir, Cu, Mg, and Ni) are included in this transformation.

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Section: Enantioselective Synthesis Of Isoindolinones By Using Organomentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Isoindolinones

Gao

Chen

Ding

et al. 2019

Chemistry An Asian Journal

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“…The best example afforded an enantioselectivity of 74 % with only 31 % yield, and 30 mol % of phosphoric acid 42 have been needed to influence this outcome. This team was further successful with intermolecular alkylation transformations employing indoles as nucleophiles, attaining the alkylation compounds with fair to satisfactory chemical yields and ee . The best results were provided at ambient temperature with tetrahydrofuran as solvent and a little loading of 2.5–5 mol % of catalyst 42 (Scheme ).…”

Section: Organocatalyzed Asymmetric Friedel‐crafts Reactions Usingmentioning

confidence: 99%

Organocatalyzed Asymmetric Friedel‐Crafts Reactions: An Update

Heravi

Zadsirjan

Heydari

et al. 2019

The Chemical Record

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The Friedel‐Crafts alkylation (F‐CA) reaction is a special kind of carbon−carbon bond formations, which is frequently being used for the formation of such bond in some aromatic rings in organic synthesis. Its asymmetric variant gives enantiorich products. Commonly, an in situ organocatalyzed asymmetric Friedel‐Crafts alkylation (AF‐CA) proceeds via generation of an enamine as an intermediate. The organocatalyzed‐AF‐CA was discovered and established in the mid‐1980s and reviewed comprehensively in 2010. In this report, we are trying to update the applications of novel organocatalysts in the AF‐CA as a versatile synthetic strategy, which is frequently used in the effective asymmetric synthesis of complex molecules, pharmaceutically important compounds and most importantly in the total synthesis of biologically active natural products.

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“…The Lete group was more successful with intermolecular alkylation reactions using indoles as nucleophiles, obtaining the alkylation products with fair to good yields and enantioselectivities (Scheme 15). 32 Optimal results were achieved at room temperature with THF as solvent and a low loading of 2.5e5 mol % of catalyst 3.…”

Section: No-acetalsmentioning

confidence: 99%