Ein chiraler Phenoxyamin‐Magnesium‐Katalysator für die enantioselektive Hydroaminierung/Cyclisierung von Aminoalkenen und die intermolekulare Hydroaminierung von Vinylarenen. Journal of the American Chemical Society. Ruthenium-catalyzed anti-Markovnikov hydroamination of vinylarenes. Proceeding via an asymmetric hydrogen‐borrowing process, the catalysis allows racemic secondary allylic alcohols to react with various amines, affording enantiomerically enriched chiral γ‐amino alcohols with broad substrate scope and excellent enantioselectivities (68 examples, up to >99 % ee). and you may need to create a new Wiley Online Library account. Recent Innovative Strategies for the Synthesis of Amines: From CN Bond Formation to CN Bond Activation. Base‐Catalysed Intramolecular Hydroamination of Vinyl Sulfides. Rare-earth metal diisopropylamide-catalyzed intramolecular hydroamination. 12 0 obj Intermolecular Radical Mediated Anti-Markovnikov Alkene Hydroamination Using N-Hydroxyphthalimide. <> 1 Please check your email for instructions on resetting your password. Kun Wang. The cyclic trimeric phosphazene base (CTPB) showed great catalytic activity for the anti-Markovnikov stereoselective hydroamination and hydrothiolation of alkynes in good to excellent yields. Time-dependent slowly-reversible inhibition of monoamine oxidase A by N-substituted 1,2,3,6-tetrahydropyridines. Online Version of Record before inclusion in an issue. Journal of Synthetic Organic Chemistry, Japan. endobj Learn more. Ruirui Xu. Please note that to comment on an article you must be registered and logged in. uuid:6f492e89-4c65-4521-9198-e0014d24a209 Valerie Schmidt describes an intermolecular anti-Markovnikov hydroamination of alkenes. If you have previously obtained access with your personal account, please log in. Hydroamination of cinnamyl alcohol using lithium amides. Until now, there had been no general method for the intermolecular anti-Markovnikov hydroamination of unactivated alkenes with primary alkyl amines. In addition, existing methods for this type of reaction usually give the Markovnikov products (which are aminated at the higher-substituted carbon). <> Acrobat Distiller 19.0 (Windows); modified using iText 2.1.7 by 1T3XT A Highly Efficient Synthesis of a Naphthalenoid Histamine‐3 Antagonist. If you do not receive an email within 10 minutes, your email address may not be registered, Titanium‐Catalyzed Hydroaminoalkylation of Alkenes by CH Bond Activation at sp3 Centers in the α‐Position to a Nitrogen Atom. Number of times cited according to CrossRef: Enantioselective Catalysis with s‐Block Organometallics. The reaction conditions are mild and effect a range of cyclization modes to give important nitrogen-containing heterocycles. Department of Chemistry, University of Liverpool, Liverpool, L69 7ZD UK. The desired products were obtained in moderate to excellent yields. Catalytic Hydroaminoalkylation of Alkenes. <. and you may need to create a new Wiley Online Library account. t Use the link below to share a full-text version of this article with your friends and colleagues. endstream Indeed, organocatalysis … A ruthenium‐catalyzed formal anti‐Markovnikov hydroamination of allylic alcohols for the synthesis of chiral γ‐amino alcohols is presented. Examples of intramolecular hydroamination . Slow addition was observed at 25 °C with either electron‐deficient p‐chlorostyrene or secondary cyclic amines such as pyrrolidine, piperidine, or morpholine. <> Intermolecular hydroaminations of unactivated alkenes, however, can be challenging. These authors contributed equally to this work. �V�患3����Z!8�Ւ���c�;v�t��&xi4⭔Z�L���^�l˞��&�_��)�?�k�"�D?� In addition, existing methods for this type of reaction usually give the Markovnikov products (which are aminated at the higher-substituted carbon). -Symmetric Rare-Earth-Metal Aminodiolate Complexes for Intra- and Intermolecular Asymmetric Hydroamination of Alkenes endobj Thorsten.Schoen Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710062 China. Learn about our remote access options, Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710062 China. application/pdf endobj %PDF-1.3 Eine allgemeine rutheniumkatalysierte Synthese von aromatischen Aminen. Catalytic Amination for N-Alkyl Amine Synthesis. in our, Anti-Markovnikov Hydroarylation of Alkenes, Addition of 1,3-Diketones to Unactivated Alkenes, Copper-Catalyzed Hydroamination of Alkenes, Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines. 6 0 obj Robert R. Knowles, Princeton University, NJ, USA, and colleagues have developed a photocatalytic method that gives the anti-Markovnikov hydroamination products(pictured) from unactivated alkenes and primary alkyl amines. Base‐Catalyzed anti‐Markovnikov Hydroamination of Vinylarenes — Scope, Limitations and Computational Studies., http://www.wiley‐vch.de/contents/jc_2046/2007/o200700147_s.pdf. In conclusion, we have reported an intramolecular anti-Markovnikov hydroamination method using catalytic amounts of thiophenol and an organic photocatalyst promoted by visible light. 8 0 obj Comparative hydroamination of aniline and substituted anilines with styrene on different zeolites, triflate based catalysts and their physical mixtures. Alkali metal and stoichiometric effects in intermolecular hydroamination catalysed by lithium, sodium and potassium magnesiates. endobj Reactions proceeded readily at 120 °C in the absence of solvent to give selective anti‐Markovnikov addition. Please check your email for instructions on resetting your password. Ambient Moisture Accelerates Hydroamination Reactions of Vinylarenes with Alkali‐Metal Amides under Air. <>stream Homogeneous Catalytic Hydroamination of Alkynes and Allenes with Ammonia. Anti‐Markovnikov Hydroamination of Racemic Allylic Alcohols to Access Chiral γ‐Amino Alcohols. One‐Pot Procedure for the Synthesis of N‐Substituted 2‐(Arylmethyl)pyrrolidines from 1‐Aryl‐2‐cyclopropylalkynes and Primary Amines by a Hydroamination/Cyclopropylimine Rearrangement/Reduction Sequence. Sterically encumbered chiral amino alcohols for titanium-catalyzed asymmetric intramolecular hydroamination of aminoallenes. Anti-Markovnikov Hydroamination of Alkenes with Aqueous Ammonia by Metal-Loaded Titanium Oxide Photocatalyst J. %���� Phosphorus, Sulfur, and Silicon and the Related Elements. and you may need to create a new Wiley Online Library account. 15 0 obj Iron-Catalyzed Anti-Markovnikov Hydroamination and Hydroamidation of Allylic Alcohols. The reaction provides high selectivities for the secondary over the tertiary amine products, i.e., it avoids over-alkylation. View the article PDF and any associated supplements and figures for a period of 48 hours. The full text of this article hosted at iucr.org is unavailable due to technical difficulties. Such materials are peer reviewed and may be re‐organized for online delivery, but are not copy‐edited or typeset. Until now, there had been no general method for the intermolecular anti-Markovnikov hydroamination of unactivated alkenes with primary alkyl amines. Palladium-Catalyzed Aerobic Oxidative Hydroamination of Vinylarenes Using Anilines: A Wacker-Type Amination Pathway. If you do not receive an email within 10 minutes, your email address may not be registered, Reactions proceeded readily at 120 °C in the absence of solvent to give selective anti‐Markovnikov addition. A ruthenium‐catalyzed formal anti‐Markovnikov hydroamination of allylic alcohols for the synthesis of chiral γ‐amino alcohols is presented. Primary amines were prone to a second hydroamination reaction to form tertiary amine byproducts. An improved method for tricyanovinilation of aromatic amines under ultrasound irradiation.
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