121824-13-3Relevant academic research and scientific papers
Biomimetic 2-Imino-Nazarov Cyclizations via Eneallene Aziridination
Corbin, Joshua R.,Fernández, Israel,Ketelboeter, Devin R.,Schomaker, Jennifer M.
, p. 5568 - 5573 (2020)
Amidoallyl cations are appealing three-carbon synthons for the preparation of complex amine-containing carbocycles; however, methods to generate and utilize these reactive species are limited and underexplored compared to those for oxallyl cations. Here we disclose a bioinspired strain-driven ring opening of bicyclic methyleneaziridines to 2-amidopentadienyl cation intermediates that readily engage in Nazarov cyclizations. Advantages of this strategy include ease of generation and improved reactivity compared to 3-pentadienyl cations, control over the ultimate position of the alkene, the potential for high dr between vicinal stereocenters, and the ability to further elaborate the products to fully substituted aminocyclopentanes. Experimental and computational studies support a dual role for the Rh2Ln complex as both a nitrene transfer catalyst and a Lewis acid promoter, insight that provides a framework for the future development of asymmetric 2-imino-Nazarov cyclizations.
AN EFFICIENT CYCLOPENTENONE FORMATION VIA AN ALLENE OXIDE
Kim, Seong Jin,Cha, Jin K.
, p. 5613 - 5616 (2007/10/02)
A new and efficient cyclopentenone annulation reaction has been developed.The annulation involves the in situ epoxidation of vinyl allenes 1a-f to furnish cyclopentenones 2a-f in 40-70percent yield.This reaction closely resembles the proposed biosynthetic route to prostanoids.
