Robust synthesis of N-sulfonylazetidine building blocks via ring contraction of α-bromo N-sulfonylpyrrolidinones.
A simple and robust one-pot nucleophilic addition-ring contraction of α-bromo N-sulfonylpyrrolidinones has been achieved toward α-carbonylated N-sulfonylazetidines. In the presence of potassium carbonate, various nucleophiles, such as alcohols, phenols or anilines, have been efficiently incorporated into the azetidine derivatives. Moreover, the α-bromopyrrolidinone precursors could be selectively obtained in good yields by monobromination of cheap and easily available N-sulfonyl-2-pyrrolidinone derivatives.
Laboratoire de Synthèse, Réactivité Organiques et Catalyse, Institut de Chimie, UMR 7177-CNRS, Université de Strasbourg, 4 rue Blaise Pascal, 67070 Strasbourg, France.
Nicolas
N
Kern
Laboratoire de Synthèse, Réactivité Organiques et Catalyse, Institut de Chimie, UMR 7177-CNRS, Université de Strasbourg, 4 rue Blaise Pascal, 67070 Strasbourg, France.
Anne-Sophie
AS
Felten
Laboratoire de Synthèse, Réactivité Organiques et Catalyse, Institut de Chimie, UMR 7177-CNRS, Université de Strasbourg, 4 rue Blaise Pascal, 67070 Strasbourg, France.
Jean-Marc
JM
Weibel
Laboratoire de Synthèse, Réactivité Organiques et Catalyse, Institut de Chimie, UMR 7177-CNRS, Université de Strasbourg, 4 rue Blaise Pascal, 67070 Strasbourg, France.
Patrick
P
Pale
Laboratoire de Synthèse, Réactivité Organiques et Catalyse, Institut de Chimie, UMR 7177-CNRS, Université de Strasbourg, 4 rue Blaise Pascal, 67070 Strasbourg, France.
Aurélien
A
Blanc
D000438:Alcohols / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry; D011760:Pyrrolidinones / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry
D000438:Alcohols; D000814:Aniline Compounds; D001384:Azetidines; D006842:Hydrocarbons, Brominated; D010636:Phenols; D011760:Pyrrolidinones; D013450:Sulfones; C028537:2-pyrrolidone