Tetrahedron

Silicon-assisted synthesis of bridged azabicyclic systems via N-acyliminium intermediates

WJ Klaver, H Hiemstra, WN Speckamp

Index: Klaver, Wim J.; Hiemstra, Henk; Speckamp, W. Nico Tetrahedron, 1988 ,  vol. 44,  # 21  p. 6729 - 6738

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Citation Number: 9

Abstract

Intramolecular acid-mediated reactions of 2-propynyl-and allylsilanes with five-and six- membered cyclic N-acyliminium ion precursors lead to bridged azabicyclic compounds (Table I). Neat formic acid is the reaction medium of choice in most cases. The cyclization reactions take place with complete regioselectivity. 2-Propynylsilanes are more reactive than allylsilanes. An ordinary olefin reacts poorly. The cyclization products can be useful for the ...