Dienamines as Diels-Alder dienes. A novel benzannulation sequence

Diels-Alder reactions of 1-amino-1,3-dienes and related systems

“…Snowden's group [13][14][15][16][17] studied the DA reaction of (E)-dienamines with different dienophiles as strategy for the synthesis of decalines and drimanes. In Scheme 3 is described the thermal cycloaddition of dienamine 19 with dimethyl fumarate to provide diastereoselectively a ≥20:1 mixture of adducts 20, which under heating eliminates dimethylamine to provide mainly decaline 21 precursor of drimane sesquiterpenes [17].…”

Platform approach to diversification: bio-based methyl coumalate to functionalized aromatics via a Diels-Alder strategy

“…Selected strategies to generate functionalized aromatic systems. [49][50][51][52][53][54] As the dienophiles became more electron-rich, the regioselectivity and yields improved accordingly based on the effective match between the partners for the IEDDA reaction.…”

“…The cyclic ketal 39e from cyclohexanone undergoes the same in situ elimination to afford tetrahydronaphthalene 40e in 81% yield. Multiple routes have employed 40e as a target through a three-step synthesis, 49 a dienamine Diels-Alder reaction, 50 and cycloaromatization with sulfide intermediates. 51 Scheme 10.…”

“…47 Aromatic systems have been functionalized in a controlled manner through electrophilic substitution of lesssubstituted aromatic precursors, especially through directed ortho metalation. 48 Additionally, functionalized aromatic systems have been constructed from condensation of acyclic species, 49 cycloaromatization of radical species, 50 base-mediated ring-opening then aromatization of 2-pyrones, 51 and most popularly from pericyclic reactions (Scheme 8 Ethyl propiolate (47a) as the dienophile afforded mixtures of regioisomers when both electron-poor species were combined. The regioselectivity and yield improved significantly with the more electron-rich ethyl 2-butynoate (47b) as the dienophile.…”