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Palladium‐Catalyzed Stereoselective Intramolecular Oxidative Amidation of Alkenes in the Synthesis of 1,3‐ and 1,4‐Amino Alcohols and 1,3‐Diamines 下载免费PDF全文
Prof. Dr. Andrei V. Malkov Dr. Darren S. Lee Dr. Maciej Barłóg Dr. Mark R. J. Elsegood Prof. Dr. Pavel Kočovský 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(17):4901-4905
An efficient and practical Pd‐catalyzed intramolecular oxidative allylic amidation provides facile access to derivatives of 1,3‐ and 1,4‐amino alcohols and 1,3‐diamines. The method operates under mild reaction conditions (RT) with molecular oxygen (1 atm) as the sole reoxidant of Pd. Excellent diastereoselectivities were attained with substrates bearing a secondary stereogenic center 相似文献
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Rhodium‐Catalyzed Sequential Allylic Amination and Olefin Hydroacylation Reactions: Enantioselective Synthesis of Seven‐Membered Nitrogen Heterocycles 下载免费PDF全文
Jeffrey S. Arnold Edward T. Mwenda Prof. Dr. Hien M. Nguyen 《Angewandte Chemie (International ed. in English)》2014,53(14):3688-3692
Dynamic kinetic asymmetric amination of branched allylic acetimidates has been applied to the synthesis of 2‐alkyl‐dihydrobenzoazepin‐5‐ones. These seven‐membered‐ring aza ketones are prepared in good yield with high enantiomeric excess by rhodium‐catalyzed allylic substitution with 2‐amino aryl aldehydes followed by intramolecular olefin hydroacylation of the resulting alkenals. This two‐step procedure is amenable to varied functionality and proves useful for the enantioselective preparation of these ring systems. 相似文献
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Efficient Synthesis of Eight‐Membered Nitrogen Heterocycles from O‐Propargylic Oximes by Rhodium‐Catalyzed Cascade Reactions 下载免费PDF全文
Prof. Dr. Itaru Nakamura Yoshinori Sato Keisuke Takeda Prof. Dr. Masahiro Terada 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(33):10214-10219
Azocine derivatives were successfully synthesized from O‐propargylic oximes by means of a Rh‐catalyzed 2,3‐rearrangement/heterocyclization cascade reaction. Moreover, the chirality of the substrate was maintained throughout the cascade process to afford the corresponding optically active azocines. 相似文献
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Prakash T. Parvatkar Dr. Perunninakulath S. Parameswaran Prof. Dr. Santosh G. Tilve 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(18):5460-5489
Heterocyclic scaffolds represent the key structural subunits of many biologically active compounds. Over the last few years iodine‐mediated reactions have been extensively studied due to their low cost and eco‐friendliness. This Review covers advances in the field of iodine‐mediated synthesis of heterocyclic compounds since 2006, especially with an emphasis on mechanisms of ring formation. In this article, syntheses of different heterocycles are classified based on the manipulation of functional groups. 相似文献
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Mette Ishoey Prof. Thomas E. Nielsen 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(29):8832-8840
Metal‐catalyzed isomerization of N‐ and O‐allylic systems is emerging as an effective method to form synthetically useful iminium and oxocarbenium intermediates. In the presence of tethered nucleophiles, several recent examples illuminate this approach as a powerful strategy for the synthesis of structurally complex and diverse heterocycles. In this Concept article, we attempt to cover this area of research through a selection of recent versatile examples. 相似文献
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Benito Alcaide Prof. Dr. Pedro Almendros Dr. Rocío Carrascosa Dipl.‐Chem. Teresa Martínez del Campo Dipl.‐Chem. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(11):2496-2499
Positive discrimination : Chemo‐ and regioselective palladium‐catalyzed cycloetherification of allendiols, namely β,γ‐ and γ,δ‐allendiols, may occur by judicious choice of palladium‐catalyzed conditions owing to their potential ability to discriminate between both nucleophilic sites (see scheme).
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Haoquan Li Dr. Wanfang Li Dr. Anke Spannenberg Dr. Wolfgang Baumann Dr. Helfried Neumann Prof. Dr. Matthias Beller Prof. Dr. Xiao‐Feng Wu 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(28):8541-8544
Combining commercially available bromoanilines and bromobenzonitriles in a novel double carbonylation process allows for a straightforward synthesis of isoindolo[1,2‐b]quinazoline‐10,12‐diones. At least five different C?C and/or C?N bonds are selectively formed in this 3‐component reaction, which likely proceeds through sequential carbonylation–cyclization–isomerisation–carbonylation steps. Notably, two molecules of CO are inserted in this highly efficient palladium‐catalyzed process. 相似文献
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Lara Bianchi Dr. Gianluca Giorgi Prof. Massimo Maccagno Dr. Giovanni Petrillo Prof. Fernando Sancassan Prof. Elda Severi Dr. Domenico Spinelli Prof. Marco Stenta Dr. Cinzia Tavani Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2010,16(4):1312-1318
When Ar is a low‐aromaticity homo‐ or heterosystem, the sulfonyl‐stabilized anion of nitrobutadienes 4 (which derive from the initial ring opening of 3‐nitrothiophene) undergoes a rather surprising addition onto the aromatic ring itself, thereby leading to the construction of an unusual eight‐membered sulfur heterocycle condensed with the original Ar ring. The competitiveness of such a pathway with respect to the formation of the thiopyran ring (i.e., addition onto the nitrovinyl moiety) is favored at low temperatures, thus revealing its nature as a kinetically controlled process. 相似文献
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Palladium‐Catalyzed Oxidative Carbonylation of N‐Allylamines for the Synthesis of β‐Lactams 下载免费PDF全文
Wu Li Dr. Chao Liu Prof. Heng Zhang Keyin Ye Guanghui Zhang Wangzheng Zhang Zhengli Duan Prof. Shuli You Prof. Aiwen Lei 《Angewandte Chemie (International ed. in English)》2014,53(9):2443-2446
β‐Lactam scaffolds are considered to be ideal building blocks for the synthesis of nitrogen‐containing compounds. A new palladium‐catalyzed oxidative carbonylation of N‐allylamines for the synthesis of α‐methylene‐β‐lactams is reported. DFT calculations suggest that the formation of β‐lactams via a four‐membered‐ring transition state is favorable. 相似文献
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A New Strategy for Enantioselective Construction of Multisubstituted Five‐Membered Oxygen Heterocycles via a Domino Michael/Hemiketalization Reaction 下载免费PDF全文
Pei‐Jin Huang Xixi Song Prof. Dr. Min‐Can Wang Prof. Dr. Jun‐Biao Chang 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(34):11994-11998
A new highly enantioselective domino Michael/hemiketalization reaction of α‐hydroxyacetophenone with β,γ‐unsaturated α‐keto esters for the synthesis of 2,2,4,5‐tetrasubstituted chiral tetrahydrofurans is reported. With 2 mol % intramolecular dinuclear zinc‐AzePhenol complex prepared in situ from the reaction of multidentate semi‐azacrown ether ligand with ZnEt2, the corresponding anti‐multisubstituted tetrahydrofuran products were obtained in up to 90 % yields, and 98 % enantiomeric excess (ee) at 0 °C for 45 min. Moreover, the products were easily converted to 2,3,5‐trisubstituted 2,3‐dihydrofurans without any loss in optical activity. 相似文献
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Yasuaki Nakayama Ruriko Sekiya Hiroki Oishi Naoto Hama Miki Yamazaki Dr. Takaaki Sato Prof. Dr. Noritaka Chida 《Chemistry (Weinheim an der Bergstrasse, Germany)》2013,19(36):12052-12058
This article describes the details of two new types of Overman rearrangement from allylic vicinal diols. Starting from identical diols, both bis(imidate)s and cyclic orthoamides were selectively synthesized by simply changing the reaction conditions. Whilst exposure of the bis(imidate)s to thermal conditions initiated the double Overman rearrangement to introduce two identical nitrogen groups in a single operation (the cascade‐type Overman rearrangement), the reaction of cyclic orthoamides resulted in a single rearrangement (the orthoamide‐type Overman rearrangement). The newly generated allylic alcohols from the orthoamide‐type reaction can potentially undergo a variety of further transformations. For instance, we demonstrated an Overman/Claisen sequence in one pot. The most conspicuous feature of this method is that it offers precise control over the number of Overman rearrangements from the same allylic vicinal diols. This method also excludes the tedious protecting‐group manipulations of the homoallylic alcohols, which are necessary in conventional Overman rearrangements. All of the performed rearrangements proceeded in a completely diastereoselective fashion through a chair‐like transition state. 相似文献
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Metal‐Free Oxidative Radical Addition of Carbonyl Compounds to α,α‐Diaryl Allylic Alcohols: Synthesis of Highly Functionalized Ketones 下载免费PDF全文
Xue‐Qiang Chu Hua Meng You Zi Prof. Dr. Xiao‐Ping Xu Prof. Dr. Shun‐Jun Ji 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(51):17198-17206
A metal‐free direct alkylation of simple carbonyl compounds (ketones, esters, and amides) with α,α‐diaryl allylic alcohols is described. The protocol provides facile access to highly functionalized dicarbonyl ketones by a radical addition/1,2‐aryl migration cascade. The regioselectivity of the reaction was precisely controlled by the nature of the carbonyl compound. 相似文献