Asymmetric Synthesis of S -Trifluoromethyl Sulfoxide and Sulfoximine Pharmacophores

Na Yeon Kwon; Justin Ye; Jonathan A. Ellman

doi:10.1021/jacs.6c03062

April 27, 2026Journal of the American Chemical SocietyOpen Access

Asymmetric Synthesis of S -Trifluoromethyl Sulfoxide and Sulfoximine Pharmacophores

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Key Points

To explore and optimize the asymmetric synthesis of S-trifluoromethyl sulfoxide and sulfoximine pharmacophores.
Cleavage of acyl group to form free-NH sulfilimine
Hydrolysis via backside displacement of amine resulting in sulfoxide formation
Inversion of stereochemistry observed during the synthesis.
Successful synthesis of S-trifluoromethyl sulfoxide with clear stereochemical inversion.
Formation of sulfoximine linked to hydrolysis of sulfilimine.
Novel pathways identified for potential drug development.

Implication

Investigates the synthesis of sulfoximines in chemical processes, suggesting novel pathways for drug development.

Abstract

-acyl group is first cleaved to give the free-NH sulfilimine that then undergoes hydrolysis by backside displacement of the amine to give the sulfoxide with inversion of stereochemistry.

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Cite This Study

Kwon et al. (2026) studied this question.

synapsesocial.com/papers/69f2f0991e5f7920c6386c69 https://doi.org/10.1021/jacs.6c03062

View Full Paper

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Asymmetric Synthesis of S -Trifluoromethyl Sulfoxide and Sulfoximine Pharmacophores

Key Points

Implication

Abstract

Discussion

Cite This Study

Asymmetric Synthesis of S -Trifluoromethyl Sulfoxide and Sulfoximine Pharmacophores

Key Points

Implication

Abstract

Discussion

Cite This Study

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