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Beilstein J. Org. Chem. 2020, 16, 1456–1464, doi:10.3762/bjoc.16.121
Graphical Abstract
Figure 1: Compounds comprising a benzo[a]quinolizidine ring system.
Scheme 1: Reactions between enolizable anhydrides and imines.
Scheme 2: Mechanistic pathways for the reaction between cyclic anhydrides and imines.
Scheme 3: Retrosynthetic analysis of the target compounds.
Scheme 4: Reaction of 6,7-dimethoxy-3,4-dihydroisoquinoline (18) with anhydrides 5–8. Reagents and conditions...
Figure 2: Representative NOE interactions in cis and trans-21–24 (only one enantiomer is shown).
Scheme 5: Reaction of 1-methyl-3,4-dihydroisoquinoline (19) with anhydrides 5–7. Reagents and conditions: xyl...
Figure 3: X-ray crystal structure of products 25 and 26.
Scheme 6: Reactions of 1-alkyl-3,4-dihydroisoquinolines 19 and 20 with anhydride 8. Reagents and conditions: ...
Figure 4: Representative NOE interactions in 28 and 29.
Scheme 7: Suggested mechanism for the formation of products 25–27.