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Synlett 1990; 1990(1): 63-66
DOI: 10.1055/s-1990-20990
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Regioselective Functionalization of Medium-Ring Lactams

Timothy J. Hagen*
  • *G. D. Searle, Central Nervous System Diseases Research, Skokie, Illinois 60077, USA
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Publikationsdatum:
08. März 2002 (online)

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Substitution on the nitrogen of 5- to 9-membered ring lactams with a tert-butoxycarbonyl (t-Boc) group facilitates the reactions of α-alkylation (12 examples with N-(t-Boc)-alkanelactams), conjugate addition (6 examples with N-(t-Boc)-2-alkenelactams), and nucleophilic ring opening (6 examples with N-(t-Boc)-6-hexanelactam). Regioselectivity can be controlled due to the cyclic nature of the lactam, which can then be opened with a variety of nucleophiles to provide acyclic systems with a high degree of functionalization.