The Journal of Organic Chemistry

Intramolecular N-(acyloxy) iminium ion-alkyne cycloadditions. A new route to bicyclic. alpha.-amino ketones

MJ Fisher, LE Overman

Index: Fisher, Matthew J.; Overman, Larry E. Journal of Organic Chemistry, 1990 , vol. 55, # 5 p. 1447 - 1459

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Citation Number: 49

Abstract

The intramolecular cyclocondensation of 15 cyclic N-(acy1oxy) iminium cations containing tethered alkyne and alkene nucleophiles is reported (eqs 5 and 6). This route to heterotricyclic systems was specifically demonstrated with substrates in which the heterodiene moiety was contained in five-, six-, and seven-membered azacyclic rings. The stereochemistry of the cycloadducts (Table IV) was controlled primarily by the size and ...

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