Indolizidones and related fused heterocycles are important intermediates for the synthesis of biologically active natural products. While limited examples of accessing these motifs through transannular cyclizations have been reported, a systematic investigation of this strategy is still needed. As such, a variety of medium-sized, alkene-containing cyclic lactams have been analyzed computationally and the transannular halo-amidation of the alkene fragment has been investigated. Conformational analysis using Merck molecular force field (MMFF) was performed for halonium intermediates, transition state estimates, and bicyclic products in Spartan’18. Low energy conformations were subsequently evaluated by density functional theory (DFT) calculations at the B3LYP 6-31+G(d) level of theory using Gaussian16. The results of this computational study will be described herein and the regioselectivities of the cyclizations will be discussed.

Computational studies of the transannular cyclization of medium-ring amido alkenes

ACS Spring Meeting 2021

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.