120230-91-3Relevant academic research and scientific papers
Enhancing the scope of the Diels-Alder reaction through isonitrile chemistry: Emergence of a new class of acyl-activated dienophiles
Townsend, Steven D.,Wu, Xiangyang,Danishefsky, Samuel J.
, p. 10659 - 10663 (2012/08/08)
α,β-Unsaturated imides, formylated at the nitrogen atom, comprise a new and valuable family of dienophiles for servicing Diels-Alder reactions. These systems are assembled through extension of recently discovered isonitrile chemistry to the domain of α,β-unsaturated acids. Cycloadditions are facilitated by Et2AlCl, presumably via chelation between the two carbonyl groups of the N-formyl amide. Applications of the isonitrile/Diels-Alder logic to the IMDA reaction, as well as methodologies to modify the N-formyl amide of the resultant cycloaddition product, are described. It is expected that this easily executed chemistry will provide a significant enhancement for application of Diels-Alder reactions to many synthetic targets.
The Triplex Diels-Alder Reaction of 1,3-Dienes with Enol, Alkene, and Acetylenic Dienophiles: Scope and Utility
Akbulut, Nihat,Hartsough, David,Kim, Ji-In,Schuster, Gary B.
, p. 2549 - 2556 (2007/10/02)
The cycloaddition of an electron-rich diene to an electron-rich dienophile may be catalyzed by irradiation of a cyanoarene.This reaction is shown to proceed through an intermediate ternary excited state complex (triplex) and is therefore called th
