40365-64-8Relevant academic research and scientific papers
Palladium catalysed tetramolecular queuing cascades of aryl iodides, carbon monoxide, amines and a polymer supported allene
Grigg,MacLachlan,Rasparini
, p. 2241 - 2242 (2000)
Chemo- and regio-specific palladium catalysed four component processes, involving formation of 3 new bonds, initiated by oxidative addition of Pd(0) with aryl iodides followed by sequential incorporation of CO (1 atm), a polymer supported allene and an am
Synthesis of Decahydrocyclopentacyclo-octene Derivatives via Intramolecular Photocycloaddition of Δα,β-Butenolides and Reductive Cleavage
Baker, William R.,Senter, Peter D.,Coates, Robert M.
, p. 1011 - 1012 (1980)
Irradiation of Δα,β-butenolides bearing but-3-enyl and penta-3,4-dienyl side-chains in the γ-position, (2) and (3), effected intramolecular cycloaddition to form fused tricyclic lactones (4) and (5), respectively, as major products; reductive ring opening of the derived keto-acid (7a) and keto-ester (9) gave the octa- and deca-hydrocyclopentacyclo-octene derivatives (8) and (10) respectively.
Medium and Large N-Heterocycle Formation via Allene Hydroamination with a Bimetallic Rh(II) Catalyst
Bohman, Benjamin O.,Davis, Rhen C.,Forson, Kelton G.,McKnight, Caitlyn E.,Michaelis, David J.,Owens, Rachel N.,Smith, Stacey J.,Stillwell, Lillian R.,Wayment, Coriantumr Z.
supporting information, p. 63 - 68 (2022/01/19)
We report the synthesis of a 2-phosphinoimidazole-derived bimetallic Rh(II) complex that enables intramolecular allene hydroamination to form 7- to 10-member rings in high yield. Monometallic Rh complexes, in contrast, fail to achieve any product formatio
Rhodium-Catalyzed Asymmetric Intramolecular Hydroamination of Allenes
Berthold, Dino,Geissler, Arne G. A.,Giofré, Sabrina,Breit, Bernhard
supporting information, p. 9994 - 9997 (2019/07/04)
The rhodium-catalyzed asymmetric intramolecular hydroamination of sulfonyl amides with terminal allenes is reported. It provides selective access to 5- and 6-membered N-heterocycles, scaffolds found in a large range of different bioactive compounds. Moreover, gram scale reactions, as well as the application of suitable product transformations to natural products and key intermediates thereof are demonstrated.
Enantioselective Rhodium-Catalyzed Dimerization of ω-Allenyl Carboxylic Acids: Straightforward Synthesis of C2-Symmetric Macrodiolides
Steib, Philip,Breit, Bernhard
, p. 6572 - 6576 (2018/05/08)
Herein, we report on the first enantioselective and atom-efficient catalytic one-step dimerization method to selectively transform ω-allenyl carboxylic acids into C2-symmetric 14- to 28-membered bismacrolactones (macrodiolides). This convenient asymmetric access serves as an attractive route towards multiple naturally occuring homodimeric macrocyclic scaffolds and demonstrates excellent efficiency to construct the complex, symmetric core structures. By utilizing a rhodium catalyst with a modified chiral cyclopentylidene-diop ligand, the desired diolides were obtained in good to high yields, high diastereoselectivity, and excellent enantioselectivity.
Remote Cooperative Group Strategy Enables Ligands for Accelerative Asymmetric Gold Catalysis
Wang, Zhixun,Nicolini, Corrado,Hervieu, Cedric,Wong, Yuk-Fai,Zanoni, Giuseppe,Zhang, Liming
supporting information, p. 16064 - 16067 (2017/11/22)
An accelerative asymmetric gold catalysis is achieved for the first time via chiral ligand metal cooperation. An asymmetrically positioned remote amide group in the designed chiral binaphthyl-based ligand plays the essential role of a general base catalyst and selectively accelerates the cyclizations of 4-allen-1-ols into one prochiral allene face. The reactions are mostly highly enantioselective with achiral substrates, and due to the accelerated nature of the catalysis catalyst loadings as low as 100 ppm are allowed. With a pre-existing chiral center at any of the backbone sp3-carbons, the reaction remained highly efficient and most importantly maintained excellent allene facial selectivities regardless of the substrate stereochemistry. By using different combinations of ligand and substrate enantiomers, it is now possible to access all four stereoisomers of versatile 2-vinyltetrahydrofurans with exceedingly high selectivity. The underpinning design of this chemistry reveals a novel and conceptually distinctive strategy to tackle challenging asymmetric gold catalysis, which to date has relied on decelerative asymmetric steric hindrance approaches.
Stereoselective synthesis of chiral polycyclic indolic architectures through Pd0-catalyzed tandem deprotection/cyclization of tetrahydro-β-carbolines on allenes
Gobé, Valérian,Guinchard, Xavier
, p. 8511 - 8520 (2015/06/02)
Enantioenriched N-allyl tetrahydro-β-carbolines were prepared by chiral phosphoric acid-catalyzed Pictet-Spengler reactions. The compounds undergo Pd0-catalyzed cyclizations through a tandem deprotection/cyclization process. The regioselectivit
Copper-catalyzed borylative allyl-allyl coupling reaction
Semba, Kazuhiko,Bessho, Naoto,Fujihara, Tetsuaki,Terao, Jun,Tsuji, Yasushi
supporting information, p. 9007 - 9011 (2014/09/17)
Borylative allyl-allyl coupling using allenes, bis(pinacolato)diboron, and allyl phosphates has been developed in the presence of a copper catalyst bearing an N-heterocyclic carbene ligand. The reaction affords boryl-substituted 1,5-diene derivatives in g
Microwave-assisted palladium(0)-catalyzed alkylative cyclization of allenyl aldehydes leading to 3-substituted 3-cycloalken-1-ols
Tsukamoto, Hirokazu,Matsumoto, Tomotaka,Kondo, Yoshinori
, p. 388 - 389 (2008/10/09)
We have developed an efficient synthetic method for 3-substituted 3-cyclohexenols and -cyclopentenol based on Pd0-catalyzed alkylative, arylative, alkenylative, alkynylative, and borative cyclization reaction of allene-carbonyl compounds. Microwave irradi
Ruthenium-catalyzed two-component addition to form 1,3-dienes: Optimization, scope, applications, and mechanism
Trost,Pinkerton,Seidel
, p. 12466 - 12476 (2007/10/03)
A two component coupling of an allene and an activated olefin to form 1,3-dienes has been developed. The requisite allenes are synthesized either from terminal alkynes by a one carbon homologation using copper(I) iodide, paraformaldehyde, and diisopropyla
