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In(III)-Catalyzed 1,2-Hydrophosphorylation of 3-Alkynyl-3-hydroxyisoindolinones to 3,3-Disubstituted Isoindolinones Featuring Both Phosphoryl and Alkynyl Groups at the C3-Position.
J Org Chem
January 2025
Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, 2025 Chengluo Avenue, Chengdu 610016, P. R. China.
We report a highly regioselective 1,2-addition of P(O)-H compounds to the in situ generated β,γ-alkynyl-α-ketimine derived from 3-alkynyl-3-hydroxyisoindolinones, which provided a general protocol for the preparation of 3,3-disubstituted isoindolinones featuring both phosphoryl and alkynyl groups at a quaternary carbon center. The use of only 2-5 mol % of an inexpensive catalyst (In(ClO)·8HO or Bi(OTf)) allowed the smooth output of the desired products under mild conditions (25 °C, 0.5-24 h) with a broad substrate scope (35 examples) in up to >99% yield.
View Article and Find Full Text PDFReactivity of Anomalous Aziridines for Versatile Access to High Fsp Amine Chemical Space.
Acc Chem Res
January 2025
Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, Wisconsin 53706, United States.
ConspectusThe manipulation of strained rings is a powerful strategy for accessing the valuable chemical frameworks present in natural products and active pharmaceutical ingredients. Aziridines, the smallest N-containing heterocycles, have long served as building blocks for constructing more complex amine-containing scaffolds. Traditionally, the reactivity of typical aziridines has been focused on ring-opening by nucleophiles or the formation of 1,3-dipoles.
View Article and Find Full Text PDFRecent Advances in Asymmetric Organometallic Electrochemical Synthesis (AOES).
Acc Chem Res
January 2025
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
ConspectusIn recent years, our research group has dedicated significant effort to the field of asymmetric organometallic electrochemical synthesis (AOES), which integrates electrochemistry with asymmetric transition metal catalysis. On one hand, we have rationalized that organometallic compounds can serve as molecular electrocatalysts (mediators) to reduce overpotentials and enhance both the reactivity and selectivity of reactions. On the other hand, the conditions for asymmetric transition metal catalysis can be substantially improved through electrochemistry, enabling precise modulation of the transition metal's oxidation state by controlling electrochemical potentials and regulating the electron transfer rate via current adjustments.
View Article and Find Full Text PDFAlkoxy-Directed Dienamine Catalysis in [4 + 2]-Cycloaddition: Enantioselective Synthesis of Benzo-[3]-ladderanol.
J Am Chem Soc
January 2025
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
Despite tremendous progress of dienamine catalysis along with its application in enantioselective synthesis over nearly two decades, certain limitations, especially with respect to the regioselectivity in the dienamine generation step, continue to persist. To overcome these shortcomings of classical dienamine catalysis, we now introduce the concept of alkoxy-directed dienamine catalysis and apply it to the enantioselective arene construction by desymmetrizing -enediones through [4 + 2]-cycloaddition. Catalyzed by a diphenylprolinol silyl ether, this reaction utilizes γ-alkoxy α,β-unsaturated aldehydes as the substrate and proceeds in a highly regioselective fashion through the intermediacy of δ-alkoxy dienamine.
View Article and Find Full Text PDFCatalytic Asymmetric 1,4-Hydrocarbonation of 1,3-Enynes via Photoredox/Cobalt/Chromium Triple Catalysis.
Angew Chem Int Ed Engl
January 2025
School of Chemistry and Chemical Engineering, Frontier Scientific Center of Transformative Molecules, Shanghai key Laboratory of Chiral Drugs and Engineering, Shanghai Jiao Tong University, Shanghai Minhang, 200240, China.
A synergistic photoredox/cobalt/chromium triple catalysis system for regioselective, enantioselective, and diastereoselective 1,4-hydrocarbonation of readily available 1,3-enyne precursors was explored, providing a modular synthetic platform for various trisubstituted axially chiral allenes bearing an extra central chirality. The protocol features a broad substrate scope, good functional group tolerance, excellent selectivity, and mild reaction conditions. Furthermore, a possible reaction mechanism is proposed based on numerous control experiments and density functional theory calculations.
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