Regioselective Functionalization of Medium-Ring Lactams
- 1 January 1990
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1990 (01) , 63-66
- https://doi.org/10.1055/s-1990-20990
Abstract
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.Keywords
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