Mild deprotection of methylene acetals in combination with trimethylsilyl triflate-2,2'-bipyridyl.

نویسندگان

  • Hiromichi Fujioka
  • Kento Senami
  • Ozora Kubo
  • Kenzo Yahata
  • Yutaka Minamitsuji
  • Tomohiro Maegawa
چکیده

The facile deprotection of methylene acetal protection of diols under mild conditions is established. The combination of trimethylsilyl triflate (TMSOTf) and 2,2'-bipyridyl followed by a weakly acidic hydrolysis was effective and the substrates having acid sensitive functional groups can be tolerated under the stated conditions. The selective deprotection between methylene acetal and benzophenone ketal was achieved.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Methodology for in situ protection of aldehydes and ketones using trimethylsilyl trifluoromethanesulfonate and phosphines: selective alkylation and reduction of ketones, esters, amides, and nitriles.

A methodology for selective transformations of ketones, esters, Weinreb amides, and nitriles in the presence of aldehydes has been developed. The use of a combination of PPh(3)-trimethylsilyl trifluoromethanesulfonate (TMSOTf) promotes selective transformation of aldehydes to their corresponding, temporarily protected, O,P-acetal type phosphonium salts. Because, hydrolytic work-up following ens...

متن کامل

Chromium (VI) Based Oxidants IV, Zinc Chlorochromate Nonahydrate Zn(ClCrO3)2, 9H2O; as An Efficient and Mild Oxidizing Agent, Part 2

Zinc chlorochromate nonahydrate is easily prepared from the aqueous solution of chromium trioxide and zinc chloride in quantitative yield. This oxidant, in methylene chloride and at room temperature, oxidizes thiols to their disulfides. Acetals and thioacetals are deprotected to their corresponding carbonyl compounds. Sulfides are selectively converted to ther sulfoxides or sulfones. Arylox...

متن کامل

Oxidative Deprotection of Trimethylsilyl Ethers with Tetrabutylammonium Periodate (TBAPI) in the Presence of AlCl3 and BF3 in Aprotic Solvents

Structurally different trimethyl silyl ethers are oxidized with Bu4/NIO4 in the presence of AlCl3 and BF3 as catalysts in CH3CN and CHCl3 under reflux conditions. The corresponding carbonyl compounds are isolated in good yields.

متن کامل

Zinc triflate-benzoyl bromide: a versatile reagent for the conversion of ether into benzoate protecting groups and ether glycosides into glycosyl bromides.

A simple and efficient method is developed for the chemoselective one-pot conversion of ethers (benzyl, TBDMS and acetal) to the corresponding benzoates by zinc triflate-catalyzed deprotection and benzoylation by benzoyl bromide. In the same reaction, methyl or p-methoxyphenyl glycosides are converted into glycosyl bromides that are useful in glycosylation reactions.

متن کامل

Bismuth Triflate Catalyzed Allylation of Acetals: A Simple and Mild Method for Synthesis of Homoallyl Ethers

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...

متن کامل

ذخیره در منابع من

ذخیره در منابع من قبلا به منابع من ذحیره شده

{@ msg_add @}


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Chemical & pharmaceutical bulletin

دوره 58 3  شماره 

صفحات  -

تاریخ انتشار 2010