4.6 Article

Asymmetric Synthesis of Multi-substituted Prolines via a Catalytic 1,3-Dipolar Cycloaddition Using a Monocationic ZnIIOAc Complex of a Chiral Bisamidine Ligand, Naph-diPIM-dioxo-R

Journal

CHEMCATCHEM
Volume 12, Issue 22, Pages 5613-5617

Publisher

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

Funding

  1. JSPS KAKENHI [JP18H04250]
  2. Japan Science and Technology Agency (JST) [JPMJCR12YC]
  3. Japan Agency for Medical Research and Development (AMED) [JP18am0101099]
  4. Sumitomo Foundation

Ask authors/readers for more resources

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.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.6
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available