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Interrogation of Enantioselectivity in the Photomediated Ring Contractions of Saturated Heterocycles.
J Am Chem Soc
January 2025
Department of Chemistry, University of California, Berkeley, Berkeley, California 94720, United States.
We recently reported a chiral phosphoric acid (CPA) catalyzed enantioselective photomediated ring contraction of piperidines and other saturated heterocycles. By extruding a single heteroatom from a ring, this transformation builds desirable C(sp)-C(sp) bonds in the ring contracted products; however, the origins of enantioselectivity remain poorly understood. In this work, enantioselectivity of the ring contraction has been explored across an expanded structurally diverse substrate scope, revealing a wide range of enantioselectivities (0-99%) using two distinct CPA catalysts.
View Article and Find Full Text PDFObservation of Intricate Chiral Optical Force in a Spin-Curl Light Field.
Phys Rev Lett
December 2024
Institute of Precision Optical Engineering, School of Physics Science and Engineering, Tongji University, Shanghai 200092, China.
Harnessing chiral optical forces facilitates numerous applications in enantioselective sorting and sensing. To date, significant challenges persist in substantiating the holistic complex theorem of these forces as experimental demonstrations employ common light waves (e.g.
View Article and Find Full Text PDFAzocarboxamide-enabled enantioselective regiodivergent unsymmetrical 1,2-diaminations.
Nat Commun
November 2024
College of Chemistry, Zhengzhou University, Zhengzhou, 450001, China.
Enantioenriched unsymmetrical vicinal diamines are important basic structural motifs. While catalytic asymmetric intermolecular 1,2-diamination of carbon-carbon double bonds represents the most straightforward approach for preparing enantioenriched vicinal-diamine-containing heterocycles, these reactions are often limited to the installation of undifferentiated amino functionalities through metal catalysis and/or the use of stoichiometric amounts of oxidants. Here, we report organocatalytic enantioselective unsymmetrical 1,2-diaminations based on the rational design of a bifunctional 1,2-diamination reagent, namely, azocarboxamides (ACAs).
View Article and Find Full Text PDFChiral Differentiation of Chiral Lactides and Chiral Diketones on Native and Phenylcarbamoylated Cyclodextrin Chiral Stationary Phases.
Chirality
December 2024
School of Science, Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Tianjin University, Tianjin, China.
Inclusion complexation, hydrogen bonds, π-π interaction, dipole-dipole interaction, and steric hindrance effect all contribute to the enantioseparation ability of cyclodextrin (CD) or CD derivatives. In this work, one native cationic CD chiral stationary phases (SHCDCSP) and four derivatized CD-CSPs, namely, per(4-trifluoromethyl) phenylcarbamoylated-β-CD CSP (SFPhCDCSP), per(4-chloro) phenylcarbamoylated-β-CD CSP (SCPhCDCSP), per(4-bromo) phenylcarbamoylated-β-CD CSP (SBPhCDCSP), and per(4-methyl) phenylcarbamoylated-β-CD CSP (SMPhCDCSP), were prepared via thioether linkage and applied for the enantioseparation of chiral lactides and chiral diketones in both reverse phase (RP) and normal phase (NP) modes. Most of the studied chiral lactides were found to be well resolved (R > 1.
View Article and Find Full Text PDFPd(ii)-catalyzed enantioselective C-H olefination and photoregulation of sterically hindered diarylethenes.
Chem Sci
December 2024
Key Laboratory for Advanced Material, Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Shanghai Key Laboratory of Functional Materials Chemistry, Institute of Fine Chemicals, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology Shanghai 200237 China
Article Synopsis
- Sterically hindered diarylethenes with intrinsic chirality have potential for regulating chiral signals and controlling liquid crystals using light, as they can change properties through unique phototransformations.
- Traditional methods for creating these chiral structures face challenges like limited separation efficiency and production scale, requiring advanced techniques like chiral HPLC.
- This study introduces a new enantioselective olefination method to create intrinsic chiral diarylethenes directly from prochiral compounds, yielding high enantioselectivity and allowing for effective photoregulation in liquid crystals with excellent stability and minimal disorder.
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