Stereochemical Tuning in CF3-Sulfinyl Transfer: Glucose-Derived Sulfinates Toward Chiral Sulforaphane Isosteres
Open Access
- 30 October 2026
- conference paper
- Published by MDPI AG in Chemistry Proceedings
- Vol. 22 (1) , 104
Abstract
Glucose-derived chiral auxiliaries were investigated as stereodivergent platforms for the preparation and transfer of a chiral CF3SO fragment toward fluorinated sulforaphane (SFN) isosteres. DAG-derived trifluoromethanesulfinates showed a base-dependent reversal of stereochemical preference but limited chromatographic stability. The more robust DCG auxiliary enabled the isolation of both diastereomeric trifluoromethanesulfinates. Reactivity proved strongly nucleophile-dependent: Grignard reagents promoted double substitution at sulfur, whereas 3-azidopropoxide afforded enantioenriched 3-azidopropyl trifluoromethanesulfinates in 30–35% yield and 65–70% ee. Conversion of the azide into an isothiocyanate provided a CF3-containing sulfinate isostere of SFN. These results establish glucose-derived trifluoromethanesulfinates as modular stereodivergent intermediates for fluorinated SFN analogues.Keywords
Funding Information
- Ministerio de Ciencia, Innovación y Universidades (PID2019-104767RB-I00/AEI/10.13039/501100011033)
- Ministerio de Ciencia, Innovación y Universidades (PID2022-138863OB-I00)
- Ministerio de Ciencia, Innovación y Universidades (MCIN/AEI/10.13039/501100011033/FEDER)
- US (University of Seville) (VII PPIT-US)
- Junta de Andalucía/CUII (DGP_PRED_2024_01383)
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