N-[(R)-(Fluoromethyl)oxidophenyl-λ4-sulfanylidene]-4-methyl-benzenesulfonamide

N-[(R)-(Fluoromethyl)oxidophenyl-λ4-sulfanylidene]-4-methyl-benzenesulfonamide is a novel chiral monofluoromethylenation reagent towards electrophiles such as α,β-unsaturated Weinreb amides. The reaction is general and a variety of structurally diverse α,β-unsaturated Weinreb amides can be monofluoromethylenated to give the corresponding monofluorinated cyclopropanes in good yield, with good diastereoselectivity, and with excellent enantioselectivity.

(1) Monofluoromethylenation of α,β-unsaturated Weinreb amides.

(2) Monofluoromethylenation of ketones.

[1] Jinbo Hu et al. Enantioselective Synthesis of Cyclopropanes That Contain Fluorinated Tertiary Stereogenic Carbon Centers: A Chiral α-Fluoro Carbanion Strategy. Angew. Chem. Int. Ed. 2012, 51, 6966 – 6970. doi:10.1002/anie.201202451
[2] Wei Zhang and Jinbo Hu. Efficient Synthesis and Ring-Opening Reactions of Monofluorinated Epoxides Derived from α-Fluorosulfoximines. Adv. Synth. Catal. 2010, 352, 2799 – 2804. doi:10.1002/adsc.201000499