Danishefsky’s Diene vs Rawal’s Diene in [4+2] Hetero-Diels-Alder Reactions with Aldehydes

Authors

  • Oleksii I. Shamrai Institute of Organic Chemistry of the National Academy of Sciences of Ukraine; Enamine Ltd, Ukraine
  • Evgenij V. Zarudnitskii Institute of Organic Chemistry of the National Academy of Sciences of Ukraine; National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute”, Ukraine https://orcid.org/0000-0003-2038-4243

DOI:

https://doi.org/10.24959/ophcj.25.324470

Keywords:

Danishefsky’s diene, Rawal’s diene, Diels-Alder reaction, aldehyde, pyran

Abstract

The Diels-Alder reaction remains one of the most versatile and widely employed cycloaddition strategies in synthetic organic chemistry. The development of functionalized dienes, particularly Danishefsky’s diene (DD) and Rawal’s diene (RD), has significantly expanded the synthetic potential of this reaction. A comparative analysis of these two dienes has been performed in this study; in particular their reactivity with aldehyde dienophiles, leading to pyran derivatives – key intermediates in the pharmaceutical synthesis, has been analyzed. The reactivity, scope, and reaction conditions for both dienes have been assessed. Although DD is well studied and widely used in synthetic protocols, RD exhibits higher reactivity, especially under mild thermal conditions, eliminating the need for the Lewis acid catalysis. Experimental results for eight aldehyde substrates have revealed key differences in their efficiency and scalability. The data obtained emphasize the complementary nature of DD and RD in synthetic applications, providing valuable recommendations for optimizing diene selection in complex organic transformations.

Supporting Agency

  • The author received no specific funding for this work.

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Published

2025-05-13

How to Cite

(1)
Shamrai, O. I.; Zarudnitskii, E. V. Danishefsky’s Diene Vs Rawal’s Diene in [4+2] Hetero-Diels-Alder Reactions With Aldehydes. J. Org. Pharm. Chem. 2025, 23, 22-29.

Issue

Vol. 23 No. 1 (2025)

Section

Original Researches

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