Gold(I)-catalyzed formation of furans by a Claisen-type rearrangement of ynenyl allyl ethers
نویسندگان
چکیده
A series of ynenyl allyl ethers were rearranged into polysubstituted furans in the presence of a gold(I) catalyst. It is proposed that the transformation involves a Claisen-type rearrangement that allows the efficient creation of quaternary centers under mild experimental conditions.
منابع مشابه
Towards the Ideal Synthesis of Homoallylic Ketones
Homoallylic ketones combine arguably two of the most synthetically useful functional groups in organic chemistry and are, therefore, very valuable synthetic intermediates. General methods for the synthesis of these intermediates include the allylation of carbonyl compounds via p-allyl palladium(II) complexes, the 1,4-addition of vinylmetal nucleophiles onto a,bunsaturated compounds, and the Cla...
متن کاملThe tandem intermolecular hydroalkoxylation/Claisen rearrangement.
The Au(I)-catalyzed intermolecular hydroalkoxylation of alkynes with allylic alcohols to provide allyl vinyl ethers that subsequently undergo Claisen rearrangement is reported. This new cascade reaction strategy facilitates the direct formation of γ,δ-unsaturated ketones from simple starting materials in a single step.
متن کاملZinc Catalyzed Claisen Rearrangement of Allyl Aryl Ethers to o-Allylated Phenols in Liquid Phase
A simple and efficient method is developed for the zinc catalyzed Claisen rearrangement of allyl aryl ethers to o-allyl phenols by stirring in an oil-bath at 55 °C in liquid phase. Moreover, zinc powder is re-cyclable up to six times use without much loss of significant activity. In addition to it, the products are obtained in good to excellent yields and are in a state of high purity. The stru...
متن کاملLewis 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 ...
متن کاملGold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers; synthesis of substituted 1,3-dienes.
Synthesis of substituted 1,3-dienes was achieved via gold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers. The N-heterocyclic carbene gold chloride catalyst (IPrAuCl) was superior in terms of activity and selectivity and afforded the 3,3-product in excellent yields. A proposed cation-π inter-action played a significant role in affecting the reaction rate.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره 7 شماره
صفحات -
تاریخ انتشار 2011