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Beilstein J. Org. Chem. 2017, 13, 1413–1424, doi:10.3762/bjoc.13.138
Graphical Abstract
Figure 1: The Castagnoli–Cushman reaction (CCR).
Figure 2: Assembly of hexahydropyrrolo[1,2-b]isoquinoline core via the CCR and its occurrence in natural and ...
Figure 3: Indolenine substrates 9a–t investigated in this work. aPrepared for the first time (the rest are kn...
Figure 4: Anti- and syn-diastereomers of 10 and 10'.
Figure 5: Single-crystal X-ray structure of compound 10l.
Scheme 1: Formation of unwanted products 11 and 12 in lieu of the CCR with 9p–t.
Figure 6: Typical J(H11-H11a)-values and corresponding dihedral angles for syn- and anti-diastereomers of com...
Figure 7: The difference in the 13C NMR chemical shifts of the angular methyl group between syn- and anti-dia...
Figure 8: Criteria for stereochemistry assignment of anti-10o.
Scheme 2: Syn/anti isomerization of compound 10e.
Scheme 3: Alternative mechanistic pathways for the CCR.
Scheme 4: Formation and fate of Mannich adduct 13e.
Scheme 5: Mechanistic rationale for the 13e→ syn/anti-10e conversion.
Scheme 6: Decarboxylation of anti/syn-10h.