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Diversity‐Oriented Synthesis of β‐Lactams and γ‐Lactams by Post‐Ugi Nucleophilic Cyclization: Lewis Acids as Regioselective Switch
Author(s) -
Li Zhenghua,
Sharma Upendra Kumar,
Liu Zhen,
Sharma Nandini,
Harvey Jeremy N.,
Van der Eycken Erik V.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500270
Subject(s) - chemistry , regioselectivity , lactam , adduct , ugi reaction , intramolecular force , lewis acids and bases , nucleophile , combinatorial chemistry , methylene , stereochemistry , nucleophilic addition , catalysis , medicinal chemistry , organic chemistry , isocyanide
Heterocyclic fused α‐methylene β‐lactams were successfully synthesized by a post‐Ugi In III ‐catalyzed intramolecular addition reaction. Switching from InCl 3 to AlCl 3 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.