Working together: The title reactions were achieved in high yields with high ee values (see scheme, (DHQD)2AQN=hydroquinidine(anthraquinone‐1,4‐diyl) diether). The cooperative catalysis of bis(cinchona alkaloid) and Lewis acid, particularly FeCl2, was effective for these transformations and gave the monofluoromethylation products with over 90 % ee and methylation products with up to 97 % ee.

Matter of choice: The title compound (FBDT), a cyclic analogue of 1‐fluorobis(phenylsulfonyl)methane (FBSM), was developed as a reagent for the nucleophilic monofluoromethylation of aldehydes. By choice of an appropriate base it is possible to achieve selective 1,2‐ or 1,4‐addition of FBDT to conjugated aldehydes. The method was applied to the synthesis of a fluorinated isostere of osmundalactone.

Wahlweise addiert: Die Titelverbindung (FBDT), ein cyclisches Analogon von 1‐Fluorbis(phenylsulfonyl)methan, wurde als Reagens für die nucleophile Monofluormethylierung von Aldehyden entwickelt (siehe Schema). Durch die Wahl der Base gelingt es, selektive 1,2‐ oder 1,4‐Additionen an konjugierte Aldehyde vorzunehmen. Die Methode wurde zur Synthese eines fluorierten Isosters von Osmundalacton verwendet.

No abstract

Asymmetric allylic monofluoromethylation of Morita—Baylis—Hillman products with FBSM (II) proceeds with high yields and enantioselectivities in the presence of (DHQD)2AQN organocatalyst.