Enantioselective Synthesis of Secondary Amines by Combining Oxidative Rearrangement and Biocatalysis in a One-Pot Process

Bernhard LM, Zelenska K, Takashima M, Arisawa M, Murai K, Gröger H (2024)
Journal of Organic Chemistry.

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
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Autor*in
Bernhard, Laura MariaUniBi; Zelenska, Kateryna; Takashima, Mirei; Arisawa, Mitsuhiro; Murai, Kenichi; Gröger, HaraldUniBi
Abstract / Bemerkung
This contribution describes the development of chemoenzymatic one-pot processes, which combine an oxidative rearrangement and a biotransformation catalyzed by an imine reductase (IRED), for the synthesis of highly enantiomerically enriched secondary amines, such as an aryl-substituted pyrrolidine and a benzazepine. The benefits of this chemoenzymatic one-pot approach include high overall conversions (up to >99%), high enantiomeric excesses (up to >99% ee), and a straightforward synthetic approach toward secondary amines without the need to isolate the formed intermediate. For the initial chemical reaction, namely, the oxidative rearrangement, PhI(OAc)2 in methanol is used as a non-natural reagent, whereas the enzymatic step requires only stoichiometric amounts of d-glucose along with catalytic amounts of IRED, glucose dehydrogenase (GDH), and the cofactor NADPH. This methodology, demonstrating the compatibility of a "classic" organic synthesis using a non-natural, highly reactive reagent and a subsequent biocatalytic step, can be applied for different amines as substrates, thus making this concept a versatile tool in synthetic organic chemistry in general and for enantioselective synthesis of heterocyclic secondary amines in particular.
Erscheinungsjahr
2024
Zeitschriftentitel
Journal of Organic Chemistry
eISSN
1520-6904
Page URI
https://pub.uni-bielefeld.de/record/2990617

Zitieren

Bernhard LM, Zelenska K, Takashima M, Arisawa M, Murai K, Gröger H. Enantioselective Synthesis of Secondary Amines by Combining Oxidative Rearrangement and Biocatalysis in a One-Pot Process. Journal of Organic Chemistry. 2024.
Bernhard, L. M., Zelenska, K., Takashima, M., Arisawa, M., Murai, K., & Gröger, H. (2024). Enantioselective Synthesis of Secondary Amines by Combining Oxidative Rearrangement and Biocatalysis in a One-Pot Process. Journal of Organic Chemistry. https://doi.org/10.1021/acs.joc.4c00459
Bernhard, Laura Maria, Zelenska, Kateryna, Takashima, Mirei, Arisawa, Mitsuhiro, Murai, Kenichi, and Gröger, Harald. 2024. “Enantioselective Synthesis of Secondary Amines by Combining Oxidative Rearrangement and Biocatalysis in a One-Pot Process”. Journal of Organic Chemistry.
Bernhard, L. M., Zelenska, K., Takashima, M., Arisawa, M., Murai, K., and Gröger, H. (2024). Enantioselective Synthesis of Secondary Amines by Combining Oxidative Rearrangement and Biocatalysis in a One-Pot Process. Journal of Organic Chemistry.
Bernhard, L.M., et al., 2024. Enantioselective Synthesis of Secondary Amines by Combining Oxidative Rearrangement and Biocatalysis in a One-Pot Process. Journal of Organic Chemistry.
L.M. Bernhard, et al., “Enantioselective Synthesis of Secondary Amines by Combining Oxidative Rearrangement and Biocatalysis in a One-Pot Process”, Journal of Organic Chemistry, 2024.
Bernhard, L.M., Zelenska, K., Takashima, M., Arisawa, M., Murai, K., Gröger, H.: Enantioselective Synthesis of Secondary Amines by Combining Oxidative Rearrangement and Biocatalysis in a One-Pot Process. Journal of Organic Chemistry. (2024).
Bernhard, Laura Maria, Zelenska, Kateryna, Takashima, Mirei, Arisawa, Mitsuhiro, Murai, Kenichi, and Gröger, Harald. “Enantioselective Synthesis of Secondary Amines by Combining Oxidative Rearrangement and Biocatalysis in a One-Pot Process”. Journal of Organic Chemistry (2024).

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