- A novel and chemoselective transformation of alcohol silyl ethers into the corresponding tetrahydropyranyl ethers
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Direct conversion of alcohol silyl ethers into the corresponding tetrahydropyranyl (THP) ethers can be easily performed by reaction with THP acetate under the influence of a catalytic amount of tert-butyldimethylsilyl trifluoromethanesulfonate (TB-SOTf). Aliphatic TBS ether can be selectively transformed into the corresponding THP ether in the presence of phenolic TBS ether.
- Suzuki,Oriyama
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- A mild and efficient selective tetrahydropyranylation of primary alcohols and deprotection of THP ethers of phenols and alcohols using PdCl 2(CH3CN)2 as catalyst
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Primary alcohols were selectively tetrahydropyranylated in good to excellent yields at room temperature using PdCl2(CH 3CN)2 as catalyst in tetrahydrofuran (THF) in the presence of phenols, secondary, and tertiary alcohols. The tetrahydropyranyl (THP) group could be efficiently removed using PdCl2(CH 3CN)2 as catalyst in CH3CN, while other protection groups such as p-toluenesulfonyl (Ts), tert-butyldiphenylsilyl (TBDPS), benzyloxycarbonyl (Cbz), allyl, benzyl (Bn), and benzoyl (Bz) remained intact under these conditions.
- Wang, Yan-Guang,Wu, Xiao-Xing,Jiang, Zhi-Yong
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- AI(OTf)3 - A highly efficient catalyst for the tetrahydropyranylation of alcohols under solvent-free conditions
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A simple and highly efficient method has been developed for the tetrahydropyranylation of alcohols by their reaction with 3,4-dihydro-2H-pyran (DHP) using a catalytic amount (0.01-1 mol%) of aluminium triflate under solvent-free conditions. The effect of various factors like temperature, amount of the catalyst, and molar ratio of substrates on the reaction conditions has also been studied. The comparative study of tetrahydropyranylation of benzyl alcohol using various catalysts including some reported ones shows the efficiency of this catalyst.
- Kamal, Ahmed,Naseer A Khan,Srikanth,Srinivasa Reddy
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scheme or table
p. 1099 - 1104
(2009/03/11)
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- Reductive etherification of carbonyl compounds with alkyl trimethylsilylethers using polymethylhydrosiloxane (PMHS) and catalytic B(C 6F5)3
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A facile synthesis of symmetrical and unsymmetrical ethers is achieved by reductive coupling of carbonyl compounds with alkoxysilanes. This reaction is performed using inert polymethylhydrosiloxane as the hydride source and B(C 6F5)
- Chandrasekhar,Chandrashekar,Nagendra Babu,Vijeender,Venkatram Reddy
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p. 5497 - 5499
(2007/10/03)
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- A novel and efficient method for the synthesis of tetrahydropyranyl ethers catalyzed by Sc(OTf)3
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Reaction of alcohols with dihydropyran in the presence of a catalytic amount of Sc(OTf)3 provides efficiently the corresponding tetrahydropyranyl ethers. After the reaction, the catalyst can be recovered quantitatively from the aqueous media and reused without loss of the activity.
- Watahiki, Tsutomu,Kikumoto, Hisashi,Matsuzaki, Masaya,Suzuki, Takeshi,Oriyama, Takeshi
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p. 367 - 368
(2007/10/03)
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