Intramolecular Diels–Alder reaction as a key step in tandem or sequential processes: a versatile tool for the synthesis of fused and bridged bicyclic or polycyclic compounds

Recent Developments in Pd0‐Catalyzed Alkene‐Carboheterofunctionalization Reactions

“…The best results were obtained by using aromatic bromodienes, such as 9-bromoanthracene or 2-bromofuran,a lthough af ew examples of transformationsb etween sulfamides and non-aromatic dienes were described. [16] Larger rings could also be formed in good yields by using phenylenediamine derivatives 26 and 9-bromoanthracene to afford compounds 27 (Scheme 9).…”

Crystal structure and Hirshfeld surface analysis of dimethyl (1R*,3aS*,3a1 R*,6aS*,9R*,9aS*)-3a1,5,6,9a-tetrahydro-1H,4H,9H-1,3a:6a,9-diepoxyphenalene-2,3-dicarboxylate

“…Since then, the reversibility of the [4 + 2] cycloaddition was observed many times for examples of a broad range of dienes and dienophiles, including alkynes and furans (Boutelle & Northrop, 2011;Taffin et al, 2010;White et al, 2000;Marchand et al, 1998;Manoharan & Venuvanalingam, 1997;Bott et al, 1996;Bartlett & Wu, 1985). From this diversity of diene/dienophile combinations, tandem and domino reactions of the [4 + 2] cycloaddition based on acetylenic dienophiles are more interesting for the total synthesis of natural or bioactive products (Sears & Boger, 2016;Parvatkar et al, 2014;Winkler, 1996). However, the range of bis-dienes suitable for such tandem transformations is very limited and, currently, there are only a few published examples of full kinetic/thermodynamic control in the course of the tandem intramolecular [4 + 2] cycloaddition (reactions leading to either kinetically or thermodynamically controlled products, depending on temperature; Marchionni et al, 1996;Oh et al, 2010;Criado et al, 2010;Paquette et al, 1978;Visnick & Battiste, 1985).…”

IMDAV reaction between phenylmaleic anhydride and thienyl(furyl)allylamines: synthesis and molecular structure of (3aSR,4RS,4aRS,7aSR)-5-oxothieno- and (3aSR,4SR,4aRS,7aSR)-5-oxofuro[2,3-f]isoindole-4-carboxylic acids

“…Cascade transformations including one or more tandem or sequential [4 + 2] cycloaddition reactions are a useful and high-usage tool in organic synthesis (Parvatkar et al, 2014;Sears & Boger, 2016;Borisova et al, 2018). In most cases, conjugated linear or cyclic alkadienes are the starting materials for these transformations.…”