Carbohydrate Derivative from Baylis–Hillman Adduct. An Easy and Short Synthesis of 2‐Deoxy‐2‐C‐methylene‐D‐erythro‐pentono‐1,4‐lactone

Recent Contributions from the Baylis−Hillman Reaction to Organic Chemistry

“…Porto and Coelho have developed a simple methodology for the synthesis of (4 S )-hydroxy-(5 R )-hydroxymethyl-3-methylenedihydrofuran-2-one via the treatment of the minor product ( anti isomer) (obtained by the Baylis−Hillman reaction of 2,3-isopropylidene d -glyceraldehyde and methyl acrylate in the presence of DABCO) with trifluoroacetic acid (Scheme ).…”

Rapid and scalable synthesis of chiral bromolactones as precursors to α-exo-methylene-γ-butyrolactone-containing sesquiterpene lactones

“…Preparation of bromolactones. As a starting point in our investigation, we envisioned that the product of the acid-mediated hydrolysis and concomitant lactonisation of enantiopure 1, readily accessible from mannitol, [40][41][42][43][44][45][46] could be converted into a bromolactone under standard Appel conditions via 2 (scheme 2). We opted for the aqueous HCl/methanol protocol and the expected product 2 was obtained.…”

Application of Sonogashira and Baylis–Hillman Reactions with β-Trifluoromethylated Acroleins

“…The Baylis-Hillman reaction is a useful and general σ C-C bond-forming reaction providing a straight forward single-step synthetic method to form densely functionalised precursors. 20,21 Their versatility has made these multifunctionalised compounds valuable synthetic intermediates 22,23 and has also stimulated their utilisation as substrates for chemical transformation mediated by palladium, especially for Heck reactions. 24,25 In continuation of our study on α-functionalisation of cyclic enones, we now report our results on the N-methylimidazole mediated Baylis-Hillman reaction between cyclic enones and trifluoromethylated acroleins 5a-f).…”