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| http://dx.doi.org/10.1002/anie.201104487 | DOI Listing |
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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 PDFSynthesis of Sulfinamidines via Iron-Catalyzed Nitrene Transfer Reaction with Sulfenamides.
J Org Chem
December 2024
Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai, 200438, China.
An iron-catalyzed nitrene transfer reaction for the rapid synthesis of sulfinamidines from readily available sulfenamides is reported. This method features mild conditions, short reaction times, and a broad substrate scope, allowing the preparation of a variety of sulfinamidines in good to excellent yields. The synthetic utility of the sulfinamidine products was further demonstrated through their conversion to other valuable sulfur(VI) compounds, such as sulfondiimidoyl fluorides, sulfinamidiate esters, and sulfonimidamides.
View Article and Find Full Text PDFHybrid Metal Catalysts as Valuable Tools in Organic Synthesis: An Overview of the Recent Advances in Asymmetric C─C Bond Formation Reactions.
Molecules
October 2024
Department of Pharmaceutical Sciences, University of Milan, Via Venezian 21, 20133 Milano, Italy.
Carbon-carbon bond formation represents a key reaction in organic synthesis, resulting in paramount importance for constructing the carbon backbone of organic molecules. However, traditional metal-based catalysis, despite its advantages, often struggles with issues related to efficiency, selectivity, and sustainability. On the other hand, while biocatalysis offers superior selectivity due to an extraordinary recognition process of the substrate, the scope of its applicable reactions remains somewhat limited.
View Article and Find Full Text PDFChemoenzymatic multistep retrosynthesis with transformer loops.
Chem Sci
October 2024
Department of Chemistry, Biochemistry and Pharmaceutical Sciences, University of Bern Freiestrasse 3 3012 Bern Switzerland
Integrating enzymatic reactions into computer-aided synthesis planning (CASP) should help devise more selective, economical, and greener synthetic routes. Herein we report the triple-transformer loop algorithm with biocatalysis (TTLAB) as a new CASP tool for chemo-enzymatic multistep retrosynthesis. Single-step retrosyntheses are performed using two triple transformer loops (TTL), one trained with chemical reactions from the US Patent Office (USPTO-TTL), the second one obtained by multitask transfer learning combining the USPTO dataset with preparative biotransformations from the literature (ENZR-TTL).
View Article and Find Full Text PDFOptically Pure Co(III) Complex Absorbed by Electrochemiluminescence-Active Covalent Organic Framework as an Enantioselective Recognition Platform to Give Opposite Responses Toward Amino Alcohol Enantiomers.
ACS Appl Mater Interfaces
October 2024
Jiangsu Key Laboratory of Advanced Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.
Article Synopsis
- This study introduces a novel achiral ionic covalent organic framework (COF) that exhibits electrochemiluminescence (ECL) properties, synthesized through the Zincke reaction.
- The COF successfully detects chiral Co(III) complexes, showing significant differences in ECL responses between different amino alcohol enantiomers.
- A strong linear relationship is established between enantiomeric composition and ECL intensity, offering a reliable method for analyzing enantiomeric purity in samples.
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