Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Ring-Fused Cyclic Aminals from Tetrahydro-β-carboline-Based Dipeptide Compounds

Ring-Fused Cyclic Aminals from Tetrahydro-β-carboline-Based Dipeptide Compounds
Giuseppe Bifulco, Pietro Campiglia, Alessia Bertamino, Simona Musella, Carmine Ostacolo, Veronica Di Sarno, Gianluigi Lauro, Tania Ciaglia, Isabel M. Gomez-Monterrey
An acid- and oxidant-promoted intramolecular cyclization of a tetrahydro-β-carboline-based dipeptide has been developed to prepare new indole-fused aminoacetals. This approach involves N-acyliminium formation from readily available precursors and cyclization under mild reaction conditions. The diastereoselectivity in the formation of the products is influenced by the specific substituents of the starting reagents, which has been rationalized analyzing the energy profile of the related reactions and the relative stability of the proposed structures based on DFT computational methods.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01656

DOI: 10.1021/acs.joc.7b01656

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