Journal
CHEMCATCHEM
Volume 12, Issue 22, Pages 5613-5617Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.202001202
Keywords
1; 3-Dipolar cycloaddition; prolines; HCV inhibitor; GW873082X; Bronsted base; Lewis acid catalyst
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Funding
- JSPS KAKENHI [JP18H04250]
- Japan Science and Technology Agency (JST) [JPMJCR12YC]
- Japan Agency for Medical Research and Development (AMED) [JP18am0101099]
- Sumitomo Foundation
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A monocationic zinc acetate complex of chiral bisamidine-type bidentate ligand (R)- or (S)-Naph-diPIM-dioxo-iPr (L(R)orL(S)) catalyzes a 1,3-dipolar cycloaddition between tridentate-type imino esters and acrylates in the absence of an external base to give the corresponding multi-substituted prolines with high reactivity, diastero-/enantio-/regio-selectivity, productivity, and broad generality. An anionic acetate ligand of the Lewis acidic Zn complex acts as a Bronsted base to facilitate a smooth intramolecular deprotonation to generate an iminoN,O-cis-Zn enolate. The oxygen atoms of two dioxolanes of theL(R)/L(S)ligand form aC(2)chiral scaffold that coordinates the Zn enolate via a non-bonding n-pi* interaction. This view is supported by the lack of enantioselectivity obtained with an sp(2)N-based Ph-BOX ligand that has no oxygen atom in the reaction site.
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