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Short Paper | Special issue | Vol 103, No. 1, 2021, pp.526-543
Published online, 13th November, 2020
DOI: 10.3987/COM-20-S(K)38
De Novo Approach to Izidines via A Gold-Catalyzed Hydroamination–N-acyliminium Ion Cyclization of Acyclic Ynamides

Kenji Sugimoto,* Shota Mizuno, Misaki Shirato, Kosuke Tanabe, and Yuji Matsuya*

*Faculty of Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama, 930-0194, Japan.

Abstract

A gold(I)-catalyzed novel domino reaction of acyclic ynamides yielding nitrogen-fused bicyclic skeletons was described. The reaction with 10 mol% JohnPhosAuNTf2 and stoichiometric amount of PhCO2H enables constructions of quinolizidine and indolizidine skeleton having tetrasubstituted carbon center. Especially in the case of quinolizidine synthesis, the quaternary stereogenic center could be furnished under highly diastereoselective manner.