The stabilized iminium catalyzed (E)-polyene cyclization: trapping of non-activated terminating groups enabled by cation

The stabilized iminium catalyzed (E)-polyene cyclization: trapping of non-activated terminating groups enabled by cation–π interactions

Published:2021-07-20 Issue: Volume: Page:1-5
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Warnica Josephine M.¹¹,Gleason James L.¹¹

Affiliation:

1. Department of Chemistry, McGill University, 801 Sherbrooke W., Montreal, QC H3A 0B8, Canada.

Abstract

A cyclic hydrazide catalyst bearing a pendant anthracene catalyzes the polyene cyclization of 1,5-hexadiene-2-carboxaldehydes. Bicyclic closure proceeds in substrates with non-activated terminating groups that fail to react with simple hydrazide catalysts. Computational analysis shows that stabilization through cation–π interactions throughout the reaction sequence leads to the enhanced reactivity of the catalyst.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

https://cdnsciencepub.com/doi/pdf/10.1139/cjc-2021-0150

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