نتایج جستجو برای: substutuent effect claisen rearrangement

تعداد نتایج: 1667083  

Journal: :Organic letters 2012
Nathan W G Fairhurst Mary F Mahon Rachel H Munday David R Carbery

The Ireland-Claisen [3,3]-sigmatropic rearrangement has been used to access biologically important β,β'-dihydroxy α-amino acids. The rearrangement reported is highly stereoselective and offers excellent levels of remote stereocontrol. This strategy has been used to synthesize the natural immunosuppressant mycestericin G and ent-mycestericin G, allowing for a revision of absolute configuration o...

Journal: :Chemical communications 2005
Donald Craig Nikolay K Slavov

First-order rate constants have been determined for the decarboxylative Claisen rearrangement reactions at 293 K of substituted methyl (E)-3-phenyl-2-propenyl 2-tosylmalonate esters, which show a linear free-energy relationship indicative of the development of positive charge on the benzylic position in the sigmatropic rearrangement transition-state.

Journal: :Organic & biomolecular chemistry 2014
Venkatesan Srinivasadesikan Jiun-Kuang Dai Shyi-Long Lee

The mechanism of aryl propargyl ether Claisen rearrangement in gas and solvent phase was investigated using DFT methods. Solvent phase calculations are carried out using N,N-diethylaniline as a solvent in the PCM model. The most favorable pathways involve a [3,3]-sigmatropic reaction followed by proton transfer in the first two steps and then deprotonation or [1,5]-sigmatropic reaction. Finally...

Journal: :Beilstein Journal of Organic Chemistry 2005
Kenny Tenza Julian S Northen David O'Hagan Alexandra MZ Slawin

BACKGROUND Asymmetric introduction of fluorine alpha-to a carbonyl has become popular recently, largely because the direct fluorination of enolates by asymmetric electrophilic fluorinating reagents has improved, and as a result such compounds are becoming attractive synthons. We have sought an alternative but straightforward asymmetric method to this class of compounds, utilising the zwitterion...

Journal: :Organic & biomolecular chemistry 2012
Y Suman Reddy Pavan K Kancharla Rashmi Roy Yashwant D Vankar

Synthesis of isofagomine has been achieved by implementation of aza-Claisen rearrangement of 2-C-hydroxymethyl glycals as a key step. The above rearrangement has also been utilized in the synthesis of biologically important polyhydroxylated piperidine frameworks such as isogalactofagomine, ent-isogalactofagomine and their analogues and some other azasugars as glycosidase inhibitors.

Journal: :Chemical communications 2008
Donald Craig Federica Paina Stephen C Smith

Microwave-assisted double decarboxylative Claisen rearrangement of bis(allyl) 2-tosylmalonates provides substituted 1,6-heptadienes, which may be alkylated, and then converted into pyridines by ozonolysis followed by reaction with ammonia generated in situ under microwave conditions.

Journal: :Organic & biomolecular chemistry 2008
Jonathan W Burton Edward A Anderson Paul T O'Sullivan Ian Collins John E Davies Andrew D Bond Neil Feeder Andrew B Holmes

The synthesis of five fused-bicyclic medium-ring lactones carrying identical ring-fusion to that in the polyether toxins is described using an enolate hydroxylation, intramolecular hydrosilation, Claisen rearrangement sequence.

Journal: :Tetrahedron 2010
David B Freeman Alexandra A Holubec Matthew W Weiss Julie A Dixon Akio Kakefuda Masami Ohtsuka Munenori Inoue Rishi G Vaswani Hidenori Ohki Brian D Doan Sarah E Reisman Brian M Stoltz Joshua J Day Ran N Tao Noah A Dieterich John L Wood

Described is the construction of the N-methylwelwitindolinone C core via an efficient strategy that employs a sequential rhodium carbenoid-mediated O-H insertion, Claisen rearrangement and transannular [3+2] nitrone cycloaddition.

Journal: :Chemical communications 2006
Seiichi Inoue Riyoung Kim Yujiro Hoshino Kiyoshi Honda

The substituted tricyclic pyrano[2,3-e]isoindolin-3-ones and , as the core structure of stachybotrin A, B, and C (), have been regioselectively synthesized for the first time by a short route which involved Mannich reaction and Claisen rearrangement.

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