Subjection of N-alkenylimides to Kulinkovich cyclopropanation conditions led to different types of N,O-acetals, which were used as precursors
for tertiary N-acyliminium ion chemistry. In this way, a variety of bi- and tricyclic lactams were efficiently synthesized.
Treatment of a variety of N-acyliminium ion precursors with 2,3-butadienyl(trimethyl)silane and related allenes in the presence of BF(3).OEt(2) provides good yields of N-protected 2-(aminomethyl)-substituted 1,3-dienes, which prove to be useful substrates for subsequent Diels-Alder and alkene metathesis reactions. [reaction: see text]
Olefination
Olefination O 0284Allenylmethylsilanes as Nucleophiles in N-Acyliminium Ion Chemistry. -BF 3 -mediated treatment of N-acyliminium ions with allenylmethylsilanes offers an efficient approach to dienelactones and 2-(aminomethyl)-substituted 1,3-dienes which are useful substrates for ring-closing metathesis and Diels-Alder reactions. -(MENTINK, G.; VAN MAARSEVEEN, J. H.; HIEMSTRA*, H.; Org. Lett. 4 (2002) 20, 3497-3500; Inst. Mol. Chem., Univ. Amsterdam, NL-1018 WS Amsterdam, Neth.; Eng.) -Jannicke 11-055 2003 Olefination
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