An MD/QM Study of the Chorismate Mutase-Catalyzed Claisen Rearrangement Reaction

2001 ◽  
Vol 105 (29) ◽  
pp. 7087-7095 ◽  
Author(s):  
Sharon E. Worthington ◽  
Adrian E. Roitberg ◽  
Morris Krauss
Keyword(s):  
Claisen Rearrangement ◽  
Chorismate Mutase ◽  
Rearrangement Reaction

A Tandem Cope-Claisen Rearrangement Reaction of meso-3,3'-Diphenylleucoisoindigos

Heterocycles ◽  
1992 ◽  
Vol 33 (1) ◽  
pp. 127 ◽  
Author(s):  
Yutaka Morita ◽  
Tetsuo Suyama ◽  
Takeshi Kato ◽  
Hiroshi Miyamae
Keyword(s):  
Claisen Rearrangement ◽  
Rearrangement Reaction

A facile synthetic route to poly(p-phenylene terephthalamide) with dual functional groups

2014 ◽  
Vol 50 (69) ◽  
pp. 9929-9931 ◽  
Author(s):  
Shuming Du ◽  
Wenbin Wang ◽  
Yan Yan ◽  
Jie Zhang ◽  
Ming Tian ◽  
...  
Keyword(s):  
Interfacial Adhesion ◽  
Claisen Rearrangement ◽  
Interface Structure ◽  
Fiber Reinforced Composites ◽  
Hydroxyl Groups ◽  
Reinforced Composites ◽  
Synthetic Route ◽  
Kevlar Fiber ◽  
Dual Functional ◽  
Rearrangement Reaction

Claisen rearrangement reaction introduces simultaneously allyl and hydroxyl groups to PPTA chains, and improves the interface structure and interfacial adhesion of Kevlar fiber reinforced composites.

Facile access to 2,2-disubstituted indolin-3-ones via a cascade Fischer indolization/Claisen rearrangement reaction

2017 ◽  
Vol 53 (54) ◽  
pp. 7485-7488 ◽  
Author(s):  
Zilei Xia ◽  
Jiadong Hu ◽  
Yu-Qi Gao ◽  
Qizheng Yao ◽  
Weiqing Xie
Keyword(s):  
Claisen Rearrangement ◽  
Fischer Indolization ◽  
Rearrangement Process ◽  
Rearrangement Reaction

From readily accessible arylhydrazines and allyloxyketones, 2,2-disubstituted indolin-3-ones could be obtained in good to excellent yields via a cascade Fischer indolization/Claisen rearrangement process.

Synthetic Studies toward Tubiferal A: Asymmetric Synthesis of a Model ABC-ring Compound

Synlett ◽  
2021 ◽  
Author(s):  
Yuki Yukutake ◽  
Takahiro Hiramatsu ◽  
Ryusei Itoh ◽  
Kazutada Ikeuchi ◽  
Takahiro Suzuki ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Claisen Rearrangement ◽  
Ring System ◽  
Alkylation Reaction ◽  
Ring Model ◽  
Stereoselective Addition ◽  
Stereogenic Centers ◽  
Rearrangement Reaction ◽  
Synthetic Studies ◽  
Ab Ring

Synthetic studies on an ABC-ring model of Tubiferal A, a triterpenoid isolated from the fruit bodies of the Tubifera dimorphotheca myxomycete, are described. The stereogenic centers at the angular positions were constructed through the stereoselective addition of a C-ring allylborane followed by an Eschenmoser–Claisen rearrangement reaction prior to the formation of the AB-ring system by a double intramolecular alkylation reaction of a dichloro nitrile intermediate.

Synthesis of Homoallylic Sulfones Through a Decarboxylative Claisen Rearrangement Reaction.

ChemInform ◽  
2005 ◽  
Vol 36 (22) ◽  
Author(s):  
Damien Bourgeois ◽  
Donald Craig ◽  
N. Paul King ◽  
David M. Mountford
Keyword(s):  
Claisen Rearrangement ◽  
Rearrangement Reaction

scholarly journals Exploring the Mechanism of Catalysis with the Unified Reaction Valley Approach (URVA)—A Review

Catalysts ◽  
2020 ◽  
Vol 10 (6) ◽  
pp. 691
Author(s):  
Elfi Kraka ◽  
Wenli Zou ◽  
Yunwen Tao ◽  
Marek Freindorf
Keyword(s):  
Chemical Reaction ◽  
Claisen Rearrangement ◽  
Reaction Path ◽  
Theoretical Background ◽  
Sigmatropic Rearrangement ◽  
Chorismate Mutase ◽  
Fine Tuning ◽  
Allylic Alcohols ◽  
Allyl Acetate ◽  
Heterogenous Catalysis

The unified reaction valley approach (URVA) differs from mainstream mechanistic studies, as it describes a chemical reaction via the reaction path and the surrounding reaction valley on the potential energy surface from the van der Waals region to the transition state and far out into the exit channel, where the products are located. The key feature of URVA is the focus on the curving of the reaction path. Moving along the reaction path, any electronic structure change of the reacting molecules is registered by a change in their normal vibrational modes and their coupling with the path, which recovers the curvature of the reaction path. This leads to a unique curvature profile for each chemical reaction with curvature minima reflecting minimal change and curvature maxima, the location of important chemical events such as bond breaking/forming, charge polarization and transfer, rehybridization, etc. A unique decomposition of the path curvature into internal coordinate components provides comprehensive insights into the origins of the chemical changes taking place. After presenting the theoretical background of URVA, we discuss its application to four diverse catalytic processes: (i) the Rh catalyzed methanol carbonylation—the Monsanto process; (ii) the Sharpless epoxidation of allylic alcohols—transition to heterogenous catalysis; (iii) Au(I) assisted [3,3]-sigmatropic rearrangement of allyl acetate; and (iv) the Bacillus subtilis chorismate mutase catalyzed Claisen rearrangement—and show how URVA leads to a new protocol for fine-tuning of existing catalysts and the design of new efficient and eco-friendly catalysts. At the end of this article the pURVA software is introduced. The overall goal of this article is to introduce to the chemical community a new protocol for fine-tuning existing catalytic reactions while aiding in the design of modern and environmentally friendly catalysts.

Ferrocenylimidazoline palladacycles as efficient catalysts for the aza-Claisen rearrangement reaction of allylic imidates

2008 ◽  
Vol 22 (11) ◽  
pp. 624-628 ◽  
Author(s):  
Xiuling Cui ◽  
Ji Ma ◽  
Dejian Yang ◽  
Junliang Wu ◽  
Maoping Song ◽  
...  
Keyword(s):  
Claisen Rearrangement ◽  
Rearrangement Reaction

Chemistry of Insect Antifeedants from Azadirachta indica (Part 22): Functionalisation of the Decalin Fragment of Azadirachtin via a Claisen Rearrangement Reaction

Synlett ◽  
1999 ◽  
Vol 1999 (8) ◽  
pp. 1295-1297 ◽  
Author(s):  
Steven V. Ley ◽  
Clare E. Gutteridge ◽  
Andrew R. Pape ◽  
Christopher D. Spilling ◽  
Cornelia Zumbrunn
Keyword(s):  
Azadirachta Indica ◽  
Claisen Rearrangement ◽  
Rearrangement Reaction ◽  
Insect Antifeedants
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