Impact of Silyl Enol Ether Stability on Palladium-Catalyzed Arylations. I Palladium/Brønsted Acid-Catalyzed α-Allylation of Aldehydes with Allylic Alcohols. do not need to formally request permission to reproduce material contained in this fAgOTf was used instead of AgClO4. Palladium/acetic acid-catalyzed fluoroalkylation of alkynes with monofluorinated sulfones as pronucleophiles. Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective Allylic Alkylation of Acylsilanes with Monosubstituted Allyl Substrates. Min-Hyuk Kang, Sun-Ah Lee, Na-Na Kang, Bong-Jin Moon. Allylic Alkylations with Enamine Nucleophiles. José L. Mascareñas, Rakesh Puttreddy, Ngong Kodiah Beyeh, The reaction of 1a with allyl ester 2d proceeded smoothly and the corresponding allylated product 3f was obtained in 70% yield (entry 5) [42]. Yun-Lin Liu, Fu-Min Liao, Yan-Fei Niu, Xiao-Li Zhao, Jian Zhou. Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. Gold(I)-Catalyzed Tandem Cycloisomerization and Fluorination of 1,3(4)-Enyne Esters with NFSI: One-Pot Assembly of 5-Fluoro- Cyclopentenones. However, in the present reaction system, intermediate 8 would prefer to act as a base and abstract a proton, Ha, from the α-position rather than attack the silyl group as a nucleophile, probably due to steric and electronic reasons. General procedure: The silyl enol ether (2 mmol) and alkyl halide (2.1 mmol) are successively added to a suspension of A9OCOCF3 (2.1 mmol) in dry CH2Cl2 (2 ml) with stirring under argon at -70 to 250 C (see Table). it in a third party non-RSC publication you must Manfred Braun, Panos Meletis, Mesut Fidan. Chen Xie, Yanling Dai, Haibo Mei, Jianlin Han, Vadim A. Soloshonok, Yi Pan. In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed. This article is part of the Thematic Series "Gold catalysis for organic synthesis". Highly Regio-, Diastereo-, and Enantioselective Pd-Catalyzed Allylic Alkylation of Acyclic Ketone Enolates with Monosubstituted Allyl Substrates. Direkte asymmetrische α-Allylierung von Aldehyden mit Allyalkoholen, ermöglicht durch das Zusammenwirken dreier Katalysatoren. However, the alkylation of 1a with 2a did not proceed at all with 5 mol % of TfOH. As expected, the isomerization of the double bond occurred and 3a was obtained in 80% yield. Metallkatalysierte enantioselektive Allylierungen in der asymmetrischen Synthese. Copper/Palladium-Catalyzed 1,4 Reduction and Asymmetric Allylic Alkylation of α,β-Unsaturated Ketones: Enantioselective Dual Catalysis. Fluoro-substituted ketones from nitriles using acidic and basic reaction conditions. Hiroya Kondo, Mayaka Maeno, Kazuki Hirano, Norio Shibata. Scheme 4 TIPS0 TIPS0 TIPS0 TIPS0 3 0 (39%) 22 23 (5-15%) The a-N-tosylammc yields depend on the molar ratio between the Sharpless reagent 5 and the silyl enol ether. Iridium-catalyzed regio- and enantioselective allylic alkylation of fluorobis(phenylsulfonyl)methane. Catalytic Enantioselective Difluoroalkylation of Aldehydes. Treatment of five-membered silyl enol ether, cyclopentenyloxytrimethylsilane (1b), with 2b in the presence of the gold catalyst gave the corresponding benzylated product 3b in 61% yield (entry 1). Enantioselective syntheses of indanes: from organocatalysis to C–H functionalization. Sequence‐Dependent Stereodivergent Allylic Alkylation/Fluorination of Acyclic Ketones. From allylic alcohols to α-fluoroketones. Alkylation of silyl enol ethers. Information about how to use the RightsLink permission system can be found at Day, Ryan M. McFadden, Scott C. Virgil, Helene Kolding, Jennifer L. Alleva, Brian M. Stoltz. Versatile Cu Enantioselective Pd-Catalyzed Allylation Reaction of Fluorinated Silyl Enol Ethers, Canada Research Chair in Organic and Medicinal Chemistry, Département de chimie, Université Laval, Québec, QC, Canada G1K 7P4. Diastereoselective Mannich Reactions Using Fluorinated Ketones: Synthesis of Stereogenic Carbon–Fluorine Units. Grégory Landelle, Marc-Olivier Turcotte-Savard, Laetitia Angers, and Jean-François Paquin . Thus, 1d reacted stereoselectively with 2a to yield E-3e. Interestingly, the formation of the isomeric Z-3e was not detected at all (entry 4) [41]. Gold-catalyzed alkylation of silyl enol ethera. The generated leaving compound abstracts a proton to regenerate the silyl enol ether structure. -Anisoyloxydauc-4,8-diene. Please reconnect. Due to the high leaving ability of the isocoumarin moiety of 6, the silyl enol ether 1 attacks the R group to give the intermediate 7 together with the gold complex 8 as a leaving compound [43-46]. Catalytic asymmetric detrifluoroacetylative aldol reactions of aliphatic aldehydes for construction of C-F quaternary stereogenic centers. With a cationic gold catalyst, derived from Ph3PAuCl and AgClO4, the reaction of 1a with 2a proceeded at 80 °C over 2 h and the benzylated silyl enol ether 3a was obtained in 35% yield, along with the eliminated isocoumarin 4a and recovered 2a in 32% and 65% yields, respectively (entry 1). )-2-Allyl-2-Methylcyclohexanone. Chem. en route Go to our 4 Sakurai 177 has found that dicobalt octacarbonyl is an excellent catalyst for the reaction (equation 67) and that the side reactions occurring through the use of the catalysts mentioned above (e.g. Catalytic Enantioselective Construction of Quaternary Stereocenters: Assembly of Key Building Blocks for the Synthesis of Biologically Active Molecules. Products have been easily obtained in a prevalent diastereoselectivity irrespective of salt counter-anion, aromatic ring substitution and silyl enol ether ring size. Chen Xie, Lingmin Wu, Jianlin Han, Vadim A. Soloshonok, Yi Pan. Fluorinated enol ethers: their synthesis and reactivity. On the other hand, no products were obtained from the reaction of 1a with benzyl benzoate (having no alkynyl group at the ortho-position) under similar reaction conditions. Regio- and Stereoselective Modification of Chiral α-Amino Ketones by Pd-Catalyzed Allylic Alkylation. Beilstein J. Org. Enamines: efficient nucleophiles for the palladium-catalyzed asymmetric allylic alkylation. The current protocol can also be used with substrates having no hydrogen at the α-position, such as 1f. Highly Diastereo- and Enantioselective Pd-Catalyzed Cyclopropanation of Acyclic Amides with Substituted Allyl Carbonates. ; Wang, S.-p.; Yu, J.-l.; Liu, H.-j. An efficient catalyst-free Mukaiyama-aldol reaction of fluorinated enol silyl ethers with tryptanthrin. Call for papers is open for this thematic issue. Barry M. Trost, Jiayi Xu and Thomas Schmidt. Katalytische enantioselektive Difluoralkylierung von Aldehyden. This approach, catalyzed by Rh(III), is combined with the α-arylation of ketone-derived silyl enol ethers to achieve a direct cross-coupling event. http://pubs.acs.org/page/copyright/permissions.html. Silyl enol ether Last updated February 22, 2019 The general structure of a silyl enol ether. Decarboxylative fluorination of β-Ketoacids with N-fluorobenzenesulfonimide (NFSI) for the synthesis of α-fluoroketones: Substrate scope and mechanistic investigation. Zhiwei Jiao, Jason J. Beiger, Yushu Jin, Shaozhong Ge, Jianrong Steve Zhou, and John F. Hartwig .

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