All articles of this category 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.
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Timothy J. Hagen (1990) studied this question.