We present a facile synthetic route toward a novel series of imidazolinyl-[2.2]paracyclophanol (UCD-Imphanol) ligands possessing central and planar chirality. Both sets of diastereomeric ligands were successfully purified by column chromatography. The preliminary application of this family of ligands showed excellent activities in the asymmetric Zn-catalyzed azomethine ylide cycloaddition. Enantioenriched pyrrolidines, in a substrate scope of 20 examples, were accessed in high levels of endo/exo ratios (up to >99/1) and enantioselectivities (up to >99 % ee) with excellent yields (up to 99 %) by using (S,S,S )-UCD-Imphanol/(S,S,R )-UCD-Imphanol, respectively.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9543521 | PMC |
| http://dx.doi.org/10.1002/anie.202205516 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Zinc-Catalyzed Enantioselective Formal (3+2) Cycloadditions of Bicyclobutanes with Imines: Catalytic Asymmetric Synthesis of Azabicyclo[2.1.1]hexanes.
Angew Chem Int Ed Engl
November 2024
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082, P. R. China.
The cycloaddition reaction involving bicyclo[1.1.0]butanes (BCBs) offers a versatile and efficient synthetic platform for producing C(sp)-rich rigid bridged ring scaffolds, which act as phenyl bioisosteres.
View Article and Find Full Text PDFZinc-Catalyzed Asymmetric Cascade Michael/Acyl Transfer Reaction between α-Hydroxy Aryl Ketones and Enynones.
Org Lett
March 2023
College of Chemistry and Institute of Green Catalysis, Zhengzhou University, Zhengzhou, Henan 450000, People's Republic of China.
We described herein a neoteric enantioselective cascade Michael/acyl transfer reaction of enynones and α-hydroxy aryl ketones catalyzed by dinuclear zinc cooperative catalysis. A series of structurally diverse chiral 1,5-dicarbonyl compounds were synthesized in good yields with excellent stereoselectivities. This strategy features broad substrate scope, high atom economy, as well as enynones as efficient electrophilic acyl transfer reagents in asymmetric cascade reactions for the first time.
View Article and Find Full Text PDFZinc-Catalyzed Enantioselective [3 + 3] Annulation for Synthesis of Chiral Spiro[indoline-3,4'-thiopyrano[2,3-]indole] Derivatives.
Molecules
January 2023
Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, China.
With a dinuclear zinc-ProPhenol complex as a catalyst, an efficient and novel [3 + 3] annulation of indoline-2-thiones and isatylidene malononitriles has been successfully developed via the Brønsted base and Lewis acid cooperative activation model. This practical methodology gives access to a broad range of chiral spiro[indoline-3,4'-thiopyrano[2,3-]indole] derivatives in good yields with excellent levels of enantioselectivities (up to 88% yield and 99% ee).
View Article and Find Full Text PDFObservation of Hyperpositive Non-Linear Effect in Asymmetric Organozinc Alkylation in Presence of -Pyrrolidinyl Norephedrine.
Molecules
June 2022
Institut de Physique et Chimie des Matériaux de Strasbourg, Université de Strasbourg-CNRS UMR7504, 23 rue du Loess, BP 43, CEDEX 2, 67034 Strasbourg, France.
Phenomena related to asymmetric amplification are considered to be key to understanding the emergence of homochirality in life. In asymmetric catalysis, theoretical and experimental models have been studied to understand such chiral amplification, in particular based on non-linear effects. Three decades after the theoretical demonstration that a chiral catalyst, when not enantiopure, could be more enantioselective than its enantiopure counterpart, we show here a new experimental example of nonlinear hyperpositive effect.
View Article and Find Full Text PDFZinc-Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane-Imidazoline N,O-ligands.
Angew Chem Int Ed Engl
August 2022
Centre for Synthesis and Chemical Biology (CSCB), School of Chemistry, University College Dublin (UCD), Belfield, Dublin 4, Ireland.
We present a facile synthetic route toward a novel series of imidazolinyl-[2.2]paracyclophanol (UCD-Imphanol) ligands possessing central and planar chirality. Both sets of diastereomeric ligands were successfully purified by column chromatography.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!