Formula: C10H13ClO3In 2018, Hedberg, Christinne;Estrup, Morten;Eikeland, Espen Z.;Jensen, Henrik H. published 《Vinyl Grignard-Mediated Stereoselective Carbocyclization of Lactone Acetals》. 《Journal of Organic Chemistry》published the findings. The article contains the following contents:
A novel Ferrier-type carbocyclization is reported. It involves a carbohydrate-derived lactone acetal synthesized from Me α-D-glucopyranoside, which upon treatment with excess vinylmagnesium bromide provides a highly substituted carbocyclic product as a single stereoisomer. The yield is greatly increased when N,N,N’,N’-tetramethylethylenediamine is added to the reaction mixture Optimized reaction conditions have been applied to lactone acetals derived from other carbohydrates. Based on the obtained results, a possible reaction mechanism has been proposed. Furthermore, scalability of the reaction up to 15 g scale and derivatization of the carbocyclic product has been demonstrated, including the formation of a rare trans-bicyclo[4.3.0]nonene scaffold via a ring-closing metathesis. The structure of this and all carbocyclized products were confirmed by X-ray crystallog. anal. To complete the study, the researchers used (1S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride(Chunks or pellets) (cas: 39637-74-6) .
(1S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride(Chunks or pellets) (cas: 39637-74-6 Formula: C10H13ClO3) is a chiral derivatizing agent. It can be prepared by reacting (-)-(1S,4R)-camphanic acid with thionyl chloride.
Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics