Ligand-controlled switch in diastereoselectivities: catalytic asymmetric construction of spirocyclic pyrrolidine-azetidine/oxe(thie)tane derivatives
- 30 May 2019
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- Vol. 55 (51), 7346-7349
- https://doi.org/10.1039/c9cc03589c
Abstract
An efficient catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides with four-membered ring-containing exocyclic alkenes has been developed, and either the exo or endo spirocyclic pyrrolidine-azetidine/oxe(thie)tane derivatives were diastereodivergently generated by employing Cu(I)/tBu-Phosferrox and a Cu(I)/N,O–ligand complex, respectively. Notably, various heteroatom-containing (N, O, S) exocyclic alkenes were found to be well-tolerated in this transformation.Keywords
Funding Information
- National Natural Science Foundation of China (21772038)
- Fundamental Research Funds for the Central Universities
This publication has 49 references indexed in Scilit:
- Catalytic asymmetric nucleophilic openings of 3-substituted oxetanesOrganic & Biomolecular Chemistry, 2014
- Catalytic Enantioselective 1,3-Dipolar Cycloadditions of Azomethine Ylides for Biology-Oriented SynthesisAccounts of Chemical Research, 2014
- exo-Selective construction of spiro-[butyrolactone-pyrrolidine] via 1,3-dipolar cycloaddition of azomethine ylides with α-methylene-γ-butyrolactone catalyzed by Cu(i)/DTBM-BIPHEPChemical Communications, 2013
- Asymmetric Catalysis for the Synthesis of Spirocyclic CompoundsACS Catalysis, 2013
- Catalytic Asymmetric exo′‐Selective [3+2] Cycloaddition for Constructing Stereochemically Diversified Spiro[pyrrolidin‐3,3′‐oxindole]sChemistry – A European Journal, 2012
- An exo‐ and Enantioselective 1,3‐Dipolar Cycloaddition of Azomethine Ylides with Alkylidene Malonates Catalyzed by a N,O‐Ligand/Cu(OAc)2‐Derived Chiral ComplexAngewandte Chemie-International Edition, 2011
- Catalytic asymmetric 1,3-dipolar cycloaddition of N-unprotected 2-oxoindolin-3-ylidene derivatives and azomethine ylides for the construction of spirooxindole-pyrrolidinesOrganic & Biomolecular Chemistry, 2010
- Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural productsNature Chemistry, 2010
- Zabofloxacin (DW-224a) activity against Neisseria gonorrhoeae including quinolone-resistant strainsDiagnostic Microbiology and Infectious Disease, 2008
- Spirocyclic Oxetanes: Synthesis and PropertiesAngewandte Chemie-International Edition, 2008