An improved method for condensation between alkyl sulfoximines and aldehydes enabled by carbonyl imidazolyl protecting group

Abstract Herein, we report an improved and practical synthesis of alkenyl sulfoximines via stereoselective condensation between aldehydes and alkyl sulfoximines. The employment of a carbonyl imidazolyl group as a protecting group for the imine moiety of alkyl sulfoximines could significantly expand the scope of substrates compared to a pivaloyl protecting group. Notably, this modification enabled the use of alkyl aldehydes and certain aryl aldehydes that were previously incompatible under conventional conditions.

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Publication Details

Journal
Chemistry Letters
Published
2025-09-23
DOI
https://doi.org/10.1093/chemle/upaf183
Primary Topic
Synthesis and Catalytic Reactions
Type
article
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article

An improved method for condensation between alkyl sulfoximines and aldehydes enabled by carbonyl imidazolyl protecting group

Kosuke Yasui, Masayuki Miyaoka, Koji Hirano, Yuichiro Tomishima et al.
Chemistry Letters
Synthesis and Catalytic Reactions
article

An improved method for condensation between alkyl sulfoximines and aldehydes enabled by carbonyl imidazolyl protecting group

Kosuke Yasui, Masayuki Miyaoka, Koji Hirano, Yuichiro Tomishima, H. NISHIMURA, Taiga Sakimori
article en

Abstract

Abstract Herein, we report an improved and practical synthesis of alkenyl sulfoximines via stereoselective condensation between aldehydes and alkyl sulfoximines. The employment of a carbonyl imidazolyl group as a protecting group for the imine moiety of alkyl sulfoximines could significantly expand the scope of substrates compared to a pivaloyl protecting group. Notably, this modification enabled the use of alkyl aldehydes and certain aryl aldehydes that were previously incompatible under conventional conditions.

Chemistry LettersVol. 54(10)
Osaka Gakuin University (JP), The University of Osaka (JP)
Openalex Percentile: Top 80%
Synthesis and Catalytic Reactions
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