Enantiospecific Synthesis of β-Substituted Tryptamines

Rubin, Heather N.; Hecke, Kinney Van; Mills, Jonathan J.; Cockrell, Jennifer; Morgan, Jeremy B.

doi:10.1021/acs.orglett.7b02474

Cited by 15 publications

(6 citation statements)

References 47 publications

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“…The Friedel–Crafts-type reaction of 2-arylaziridines with electron-rich (hetero)arenes represents a straightforward way to highly useful 2-(hetero)arylphenethylamines . Although the Lewis acid catalyzed racemic or enantiospecific versions of this reaction have been well documented, the catalytic enantioconvergent version has remained unknown while the Lewis acid-catalyzed kinetic resolution process has been limited to indole substrates only . Pleasingly, the above Lewis acid catalyzed enantioconvergent reaction system also works well in this reaction (Table ).…”

Section: Resultsmentioning

confidence: 99%

Lewis Acid Catalyzed Dynamic Kinetic Asymmetric Transformation of Racemic N-Sulfonylaziridines

Yang

Liu

et al. 2018

J. Am. Chem. Soc.

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The first Lewis acid catalyzed stereoconvergent transformation of racemic 2-(hetero)aryl-N-sulfonylaziridines via C−N bond cleavage with nucleophiles is presented. This includes the [3 + 2] annulations with (hetero)aromatic aldehydes and 1,3-disubstituted indoles, asymmetric Friedel− Crafts type reaction with electron-rich (hetero)arenes, and asymmetric aminolysis with amines, providing facile access to chiral 1,3-isoxazolidines, pyrroloindolines, 2-(hetero)arylphenethylamines, and vicinal diamines. This method features a simple and cheaply available complex of Cu(I)− chiral BINAP catalyst, excellent yield and high diastereo-and enantioselectivities, and mild reaction conditions. A mechanism involving type I dynamic kinetic asymmetric transformations (DyKATs) of the racemic aziridines is proposed based on the results of control experiments.

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Section: Resultsmentioning

confidence: 99%

Lewis Acid Catalyzed Dynamic Kinetic Asymmetric Transformation of Racemic N-Sulfonylaziridines

Yang

Liu

et al. 2018

J. Am. Chem. Soc.

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“…Of particular interest is the possibility to prepare enantiopure tryptamines by the regioselective and stereoinvertive ring opening of aziridines with indoles (Scheme 3). [19] …”

Section: Lewis Acidic Boron Reagentsmentioning

confidence: 99%

Boron Reagents and Catalysts for the Functionalization of Strained Heterocycles

Pineschi

2021

Adv Synth Catal

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The particular nature of boron compounds allows an ample modularity of their properties ranging from Lewis acids, C‐nucleophiles, B‐nucleophiles, or even conjunctive reagents for new synthetic manipulations. Moreover, the increasing demand for functionalized boron derivatives for pharmaceutical or material science applications requires the development of new synthetic methods for boron introduction in organic compounds. This review summarizes the possible combinations of boron derivatives with a variety of strained heterocycles reported in the most recent literature.

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“…Our interest in developing catalysts for aziridine desymmetrization began with the palladium-catalyzed rearrangement of N -acylaziridines to oxazolines . Previous success employing indoles as nucleophiles in the ring opening of N -acylaziridines compelled us to investigate the aziridine desymmetrization. Wang and co-workers reported the use of indoles to generate enantioenriched tryptamines under magnesium catalysis while our work was underway (Scheme ).…”

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confidence: 99%

Palladium-Catalyzed, Enantioselective Desymmetrization of N-Acylaziridines with Indoles

et al. 2021

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Ring opening reactions of meso-aziridines generate chiral amine derivatives where the control of stereochemistry is possible through enantioselective catalysis. We report the use of a diphosphine–palladium(II) catalyst for the highly enantioselective desymmetrization of N-acylaziridines with indoles. The β-tryptamine products are isolated in moderate to high yield across a range of indole and aziridine substitution patterns. The synthetic utility of β-tryptamine products is demonstrated by conversion to the brominated pyrroloindoline derivative.

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Enantiospecific Synthesis of β-Substituted Tryptamines

Cited by 15 publications

References 47 publications

Lewis Acid Catalyzed Dynamic Kinetic Asymmetric Transformation of Racemic N-Sulfonylaziridines

Lewis Acid Catalyzed Dynamic Kinetic Asymmetric Transformation of Racemic N-Sulfonylaziridines

Boron Reagents and Catalysts for the Functionalization of Strained Heterocycles

Palladium-Catalyzed, Enantioselective Desymmetrization of N-Acylaziridines with Indoles

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