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N-Fluorenyltryptamines as a Useful Platform for Catalytic Enantioselective Pictet–Spengler Reactions

https://doi.org/10.1055/a-1970-4452

Adili, Alafate; Sole, Aniket V.; Das, Bishwaprava; Matter, Megan E.; Seidel, Daniel (May 2023, Synthesis)

Abstract In the presence of a thiourea–carboxylic acid catalyst, N-9-fluorenyltryptamines undergo highly enantioselective Pictet–Spengler reactions with a range of aldehydes. The reaction works particularly well with aromatic aldehydes, tolerating electronically diverse substituents in all ring positions. Electron-deficient tryptamines are viable substrates. Removal of the fluorenyl protecting group is readily accomplished without deterioration of product ee.
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Degradation of Polyacrylates by One-Pot Sequential Dehydrodecarboxylation and Ozonolysis

https://doi.org/10.1021/jacs.3c02497

Korpusik, Angie B; Adili, Alafate; Bhatt, Kamal; Anatot, Jacqueline E; Seidel, Daniel; Sumerlin, Brent S (May 2023, Journal of the American Chemical Society)

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Mechanism of a Dually Catalyzed Enantioselective Oxa-Pictet–Spengler Reaction and the Development of a Stereodivergent Variant

https://doi.org/10.1021/acscatal.2c05484

Adili, Alafate; Webster, John-Paul; Zhao, Chenfei; Mallojjala, Sharath Chandra; Romero-Reyes, Moises A.; Ghiviriga, Ion; Abboud, Khalil A.; Vetticatt, Mathew J.; Seidel, Daniel (February 2023, ACS Catalysis)

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Catalytic Enantioselective Approaches to the oxa-Pictet–Spengler Cyclization and Other 3,6-Dihydropyran-Forming Reactions

https://doi.org/10.1055/s-0039-1690686

Zhu, Zhengbo; Adili, Alafate; Zhao, Chenfei; Seidel, Daniel (July 2019, SynOpen)

This Short Review provides an analysis of the state-of-the-art in catalytic enantioselective oxa-Pictet–Spengler cyclizations. Also discussed are other catalytic reactions providing access to enantioenriched isochromans and tetrahydropyrano[3,4-b]indoles. Context is provided and remaining challenges are highlighted.
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Catalytic Enantioselective [4+2] Cycloadditions of Salicylaldehyde Acetals with Enol Ethers

https://doi.org/10.1002/anie.202315759

Hu, Xiaojun; Zhu, Zhengbo; Li, Zhongzheng; Adili, Alafate; Odagi, Minami; Abboud, Khalil A.; Seidel, Daniel (December 2023, Angewandte Chemie International Edition)

Abstract A readily accessible conjugate‐base‐stabilized carboxylic acid (CBSCA) catalyst facilitates highly enantioselective [4+2] cycloaddition reactions of salicylaldehyde‐derived acetals and cyclic enol ethers, resulting in the formation of polycyclic chromanes with oxygenation in the 2‐ and 4‐positions. Stereochemically more complex products can be obtained from racemic enol ethers. Spirocyclic products are also accessible.
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Photocatalytic Direct Decarboxylation of Carboxylic Acids to Derivatize or Degrade Polymers

https://doi.org/10.1002/anie.202209085

Adili, Alafate; Korpusik, Angie B.; Seidel, Daniel; Sumerlin, Brent S. (September 2022, Angewandte Chemie International Edition)

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