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Exocyclic bromination of N-substituted β- and γ-lactams

✍ Scribed by Christopher J. Easton; Michael J. Pitt

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
245 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

Regioselective halogenation of the N-susbtituted lactams (3a)-(3d) affords the corresponding exocyclic bromides (4a)-(4d). The procedure provides a novel alternative mute to N-(c&aloaJkyl)-substituted lactams, which are of particular interest in the synthesis of g-lactam antibiotics.

Reactions of N-substituted p-and y-lactams at exocyclic carbon adjacent to amide nitrogen are complicated by competing reactions at the corresponding endocyclic position.14 For example, the copper-catalysed reaction of (la) with t-butyl perbenzoate afforded (lb) and

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