Diastereoselective ring cleavage of azetidines with cyanogen bromide

Melvin Raulin (1) , Bruno Drouillat (1) , Jérome Marrot (1) , François Couty (1) , Karen Wright (1)

1 ILV - Institut Lavoisier de Versailles

N-alkyl azetidines bearing a chiral substituent at the nitrogen atom, and a variable substituent at C-3 as a prochiral centre, react readily with cyanogen bromide even at low temperatures to produce the corresponding 3-bromo-N-cyanamides as diastereoisomeric mixtures via ring opening. This reaction was found to be diastereoselective (up to 80:20 dr). In one case, the major diastereomer could be isolated by recrystallization, and the configuration of the newly created stereocentre was determined by X-ray crystallography.

Mots clés: Azetidines; Cyanamides; Diastereoselectivity; Ring cleavage

Domaines: Chimie organique

Melvin Raulin, Bruno Drouillat, Jérome Marrot, François Couty, Karen Wright. Diastereoselective ring cleavage of azetidines with cyanogen bromide. Tetrahedron Letters, 2022, 94, pp.153710. ⟨10.1016/j.tetlet.2022.153710⟩. ⟨hal-03642654⟩