Cesium fluoride-mediated claisen rearrangement of aryl propargyl ether and its application to the synthesis of chelerythrine.
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چکیده
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Quantum mechanistic insights on aryl propargyl ether Claisen rearrangement.
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...
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The propargyl Claisen rearrangement is a known protocol to gain access to functionalized allenes through the [3,3]-sigmatropic transformation of propargyl vinyl ethers. The correct use of appropriate propargyl vinyl ethers as starting materials coupled with suitable reaction conditions can aid in the development of new domino methodologies in which the allenes are valuable intermediates in rout...
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Lewis Acid Mediated Claisen-Type Rearrangement of Aryl Dienyl Ethers
The Claisen rearrangement and its applications to organic synthesis have been studied for a long time.l In recent years, this rearrangement has been applied in stereocontrolled natural product synthesis2 and asymmetric i n d ~ c t i o n . ~ The term "Claisen rearrangement", which originally denoted the rearrangement of allyl aryl ethers to 0or p-allylphenols, has now been extended to analogous ...
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ژورنال
عنوان ژورنال: Chemical and Pharmaceutical Bulletin
سال: 1990
ISSN: 0009-2363,1347-5223
DOI: 10.1248/cpb.38.1775