Stereoselective NaN3-catalyzed halonitroaldol-type reaction of azetidine-2,3-diones in aqueous media.
نویسندگان
چکیده
Azetidine-2,3-diones (alpha-oxo-beta-lactams) and bromonitromethane undergo coupling in aqueous media in the presence of catalytic amounts of sodium azide. The stereoselectivity of the process was generally good, proceeding with reasonable anti : syn ratios under substrate control. On this basis, a simple and fast protocol for the synthesis of the potentially bioactive 3-substituted 3-hydroxy-beta-lactam moiety has been developed. Besides, 2-azetidinone-tethered 1-halo-1-nitroalkan-2-ols are quite useful building blocks; for example, reactions of the above nitrobromohydrins provided spiranic and fused bicyclic-beta-lactams.
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ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 6 9 شماره
صفحات -
تاریخ انتشار 2008