A convenient and chemoselective one-pot oxidation/Wittig reaction for the C2-homologation of carbohydrate-derived glycols.

نویسندگان

  • Fernando R Pinacho Crisóstomo
  • Romen Carrillo
  • Tomás Martín
  • Fernando García-Tellado
  • Víctor S Martín
چکیده

[reaction: see text] A simple and convenient one-pot protocol for the chemoselective C2-homologation of carbohydrate-derived glycols is described. The method comprises the chemoselective oxidation of the glycol to the corresponding hydroxyaldehyde and the subsequent Wittig alkenylation. In addition, the method does not need selective protective group manipulation, and it is safe, economical, fast (5 to 6 h), and bench-friendly. Its general utility is discussed.

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

An Efficient One-pot Synthesis of Dialkyl fumarates Mediated by inyltriphenylphosphonium Salt in the Intramolecular Wittig Reaction

An efficient three-component reaction of dialkyl acetylendicarboxylates and 2-Pyrrolidin in the presence of triphenylphosphine produces dialkyl 2-(2-Pyrrolidin-N-yl)-3-(triphenylphosphanylidene)succinate. These phosphoranes undergo mild intramolecular Wittig reaction to produce dialkyl (E)-2-(4,5-dihydro-3H-pyrrol-2-yl)fumarate in excellent yields.

متن کامل

A chemoselective oxidation of monosubstituted ethylene glycol: facile synthesis of optically active α-hydroxy acids.

A mild and efficient method for the synthesis of optically active α-hydroxy acids through chemoselective oxidation of monosubstituted ethylene glycols using the TEMPO-NaOCl reagent system is described. It is evident from our studies that the solvent, pH and reaction temperature are very crucial for the success of this oxidation. The versatility of this method has been demonstrated with a variet...

متن کامل

Convenient One-pot Access to Pyrano[2,3-d]pyrimidine Derivatives via a CuCl2.2H2O Catalyzed Knoevenagel-Michael Addition Reaction in Water/Ethanol Media

Convenient procedure for the synthesis of corresponding pyrano[2,3-d]pyrimidine derivatives were developed via one-pot three-component reaction of aryl aldehyde derivatives, malononitrile with barbituric acids in the presence of copper (II) chloride dihydrate (CuCl2.2H2O) as highly efficient Lewis acid catalyst. This protocol has advantages such as readily and inexpensive catalyst, high reactio...

متن کامل

Carbohydrate-based first stereoselective total synthesis of bioactive cytospolide P.

A facile carbohydrate-based highly stereoselective synthetic route has been developed for the cytospolide P (1) from D-ribose for the first time. Key steps of the synthesis include Wittig homologation, regioselective epoxide ring opening, Sharpless asymmetric epoxidation, Evans aldol reaction, and Yamaguchi macrolactonization.

متن کامل

One-pot, four-component synthesis of fully substituted 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane (Ph3PNNC), a primary amine, a carboxylic acid and cinnamaldehyde

The imine intermediate generated by the addition of primary amine to the cinnamaldehyde is trapped by the N-isocyaniminotriphenylphosphorane (Ph3PNNC) and a carboxylic acid, and leads to the formation of the corresponding iminophosphorane intermediate. The 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were comp...

متن کامل

ذخیره در منابع من


  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:
  • The Journal of organic chemistry

دوره 70 24  شماره 

صفحات  -

تاریخ انتشار 2005