This paper reports the allylic bromide rearrangement of 3-bromo-3-alkenyl-azetidin-2-ones, induced by m-chloroperbenzoic acid, N-bromosuccinimide or benzoylperoxide as radical initiators. The substitution of bromide by resin supported acids, followed by hydrolysis of the ester moiety, allowed an hydroxyl- or keto- function to be introduced in the C3 side chain of the azetidinone, thus giving access to a new class of potential cholesterol absorption inhibitors.

Introduction of hydroxyl- or keto- functionalities into the side chain of azetidin-2-ones via allylic bromide rearrangement, followed by supported reagent substitution

BENFATTI, FIDES;CARDILLO, GIULIANA;FABBRONI, SERENA;GENTILUCCI, LUCA;PERCIACCANTE, ROSSANA;TOLOMELLI, ALESSANDRA
2005

Abstract

This paper reports the allylic bromide rearrangement of 3-bromo-3-alkenyl-azetidin-2-ones, induced by m-chloroperbenzoic acid, N-bromosuccinimide or benzoylperoxide as radical initiators. The substitution of bromide by resin supported acids, followed by hydrolysis of the ester moiety, allowed an hydroxyl- or keto- function to be introduced in the C3 side chain of the azetidinone, thus giving access to a new class of potential cholesterol absorption inhibitors.
F. Benfatti; G. Cardillo; S. Fabbroni; L. Gentilucci; R. Perciaccante; A. Tolomelli
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/19411
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