Tetrahedron p. 143 - 148 (1980)
Update date:2022-08-11
Topics:
Schoemaker, H. E.
Boer-Terpstra, Tj.
Dijkink, J.
Speckamp, W. N.
Cyclisation of acetylenic ethoxylactams 1b-12b leads to bridgehead nitrogen bicyclic ketones in excellent yields.The reaction is weakly acid-catalysed and proceeds at ambient temperature.The observed regioselectivity effect is discussed in terms of stability of exo vs endo vinyl cations and ring strain effects.The high yield conversion of N-(5-hexynyl)-ethoxy lactams 7b and 8b in the 5/8 and 6/8 fused bicyclic ketolactams 7c and 8c deserves special attention.
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Doi:10.1134/S1070428014080053
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