- Enantioselective Heck Arylation of Acyclic Alkenol Aryl Ethers: Synthetic Applications and DFT Investigation of the Stereoselectivity
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Herein we report the enantioselective Heck-Matsuda arylation of acyclic E and Z-alkenyl aryl ethers. The reactions were carried out under mild conditions affording the enantioenriched benzyl ethers in a regioselective manner, moderate to good yields (up to 73%), and in good to excellent enantiomeric ratios (up to 97:3). The enantioselective Heck-Matsuda arylation has shown a broad scope (25 examples), and some key Heck-Matsuda adducts were further converted into more complex and valuable scaffolds including their synthetic application in the synthesis of (R)-Fluoxetine, (R)-Atomoxetine, and in the synthesis of an enantioenriched benzo[c]chromene. Finally, in silico mechanistic investigations into the reaction's enantioselectivity were performed using density functional theory. (Figure presented.).
- Polo, Ellen Christine,Wang, Martí Fernández,Angnes, Ricardo Almir,Braga, Ataualpa A. C.,Correia, Carlos Roque Duarte
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p. 884 - 892
(2019/12/30)
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- Synthesis of aryl α,α-difluoroethyl thioethers a novel structure motif in organic chemistry, and extending to aryl α,α-difluoro oxyethers
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A method for the preparation of aryl α,α-difluoroethyl thioethers (ArSCF2CH3) is reported and the synthesis approach is extended to aryl α,α-difluoroethyl oxygen ethers. Selected building blocks are further elaborated in cross-coupli
- Tomita, Ren,Al-Maharik, Nawaf,Rodil, Andrea,Bühl, Michael,O'Hagan, David
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supporting information
p. 1113 - 1117
(2018/02/22)
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- Metal-free oxidative cyclization of alkynyl aryl ethers to benzofuranones
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Readily available phenols can be converted into substituted aryl alkynyl ethers, which react with an N-oxide as an oxidant and catalytic amounts of a Bronsted acid to provide benzofuranones. If non-terminal alkynyl ethers are applied, a 1,2-hydride shift takes place and phenyl acrylates are obtained. Thus activated alkynes can serve as α-oxy carbene precursors even in the absence of a metal catalyst. Copyright
- Graf, Katharina,Ruehl, Carmen L.,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
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p. 12727 - 12731
(2013/12/04)
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