Diversity‐Oriented Synthesis of β‐Lactams and γ‐Lactams by Post‐Ugi Nucleophilic Cyclization: Lewis Acids as Regioselective Switch

Publisher: John Wiley & Sons Inc

E-ISSN: 1099-0690|2015|18|3957-3962

ISSN: 1434-193x

Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Vol.2015, Iss.18, 2015-06, pp. : 3957-3962

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Abstract

AbstractHeterocyclic fused α‐methylene β‐lactams were successfully synthesized by a post‐Ugi InIII‐catalyzed intramolecular addition reaction. Switching from InCl3 to AlCl3 led to the regioselective synthesis of α,β‐unsaturated γ‐lactams. Moreover, replacing terminal alkynes by substituted alkynes in the Ugi adducts resulted in the exclusive formation of γ‐lactams with both catalytic systems.