Introduction of hydroxyl- or keto- functionalities into the side chain of azetidin-2-ones via allylic bromide rearrangement, followed by supported reagent substitution
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.
Keywords: azetidinones ; allylic bromide ; rearrangement ; supported reagents ; Cholesterol Absorption Inhibitors ; Anion-Exchange Resins ; Beta-Lactams ; Stereoselective-Synthesis ; Alkyl-Halides ; Synthons ; Acid ; Stereochemistry ; 2-Azetidinones ; Epoxidation
Record created on 2011-02-06, modified on 2016-08-09