Article Dans Une Revue Tetrahedron Letters Année : 2022

Diastereoselective ring cleavage of azetidines with cyanogen bromide

Résumé

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.

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hal-03642654 , version 1 (25-07-2022)

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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⟩
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