ALLYLSILANES AS SYNTHETIC INTERMEDIATES. II. SYNTHESES OF HOMOALLYL ETHERS FROM ALLYLSILANES AND ACETALS PROMOTED BY TITANIUM TETRACHLORIDE
نویسندگان
چکیده
منابع مشابه
Lewis acid-promoted cycloaddition reaction of cyclopropanes with allylsilanes.
The treatment of cyclopropanes having donor and acceptor substituents at the vicinal positions on the cyclopropane ring with a Lewis acid readily generates a 1,3-zwitterion, which reacted with allylsilanes to produce cycloadducts and allylic products. It was found that the yield of the cycloadduct depends on the steric demand of the alkyl substituents on the silicon atom.
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The allylation of acetals using allyltrimethylsilane is efficiently catalyzed by bismuth triflate (1.0 mol%). The reaction proceeds smoothly at room temperature to afford the corresponding homoallyl ether in good yield. The mild reaction conditions, the low toxicity of bismuth salts, and the high catalytic efficiency of the system make this procedure particularly attractive for large-scale synt...
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Acyclic allylic monofluorides were prepared by electrophilic fluorination of branched (E)-allylsilanes with Selectfluor. These reactions proceeded with efficient transfer of chirality from the silylated to the fluorinated stereocentre. Upon double fluorination, an unsymmetrical ethyl syn-2,5-difluoroalk-3-enoic ester was prepared, the silyl group acting as an anti stereodirecting group for the ...
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The carboazidation of chiral allylsilanes has been investigated by varying the nature of the substituents at the silicon center and on the carbon framework. The influence of temperature and the nature of the sulfonyl azide, as well as the stereochemistry of the remote stereogenic center, on the 1,2-diastereocontrol of the process were considered. Good to excellent levels of diastereocontrol wer...
متن کاملREACTIONS OF ALLYLSILANES AND APPLICATION TO ORGANIC SYNThESIS
Abstract — Allylsilanes undergo regiospecific reactions with a variety of electrophilic species, especially with carbon electrophiles to form a new carbon—carbon bond. An electrophile enters on the terminus of the allylic system and the cleavage of the carbon—silicon bond occurs to give a new allylic system in which the double bond is relocated adjacent to its original position. Allylsilanes al...
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ژورنال
عنوان ژورنال: Chemistry Letters
سال: 1976
ISSN: 0366-7022,1348-0715
DOI: 10.1246/cl.1976.941