Diastereoselective synthesis of cyclopentanediols by InCl 3/Al mediated intramolecular pinacol coupling reaction in aqueous media.

نویسندگان

  • Yunhua Chen
  • Jieping Wan
  • Chunyan Wang
  • Cuirong Sun
چکیده

A "green" and practical intramolecular pinacol coupling reaction promoted by InCl 3/Al catalysts in aqueous media has been developed. Under mild conditions, a novel class of polysubstituted cyclopentane-1,2-diols have been obtained with excellent diastereoselectivity.

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

Synthesis of Differentially Protected myo- and chiro-Inositols from D-Xylose; Stereoselectivity in Intramolecular SmI(2)-Promoted Pinacol Reactions.

Methods for the enantioselective conversion of D-xylose to differentially protected myo-inositol and L-chiro-inositol have been developed. The key transformation is a highly diastereoselective intramolecular SmI(2)-promoted pinacol coupling. The stereoselectivity was extremely dependent on the conditions, suggesting a change in mechanism. Preliminary mechanistic experiments and possible explana...

متن کامل

Influence of chelating silyl scavengers on the diastereoselectivity of chromium catalyzed pinacol cross couplings

The choice of the silyl scavenger shows a substantial influence on the diastereoselectivity of the chromium catalyzed pinacol cross coupling. In the case of the intramolecular cyclization, two competing effects are observed. If the silylation reagents contain chelating heteroatoms in the side chain, a remarkable trans-selectivity is observed. Conversely the cis-diols are preferred if bulky subs...

متن کامل

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 Convenient Base-Mediated Diastereoselective Synthesis of 2-Oxo-N,4,6-triarylcyclohex-3-enecarboxamides via Claisen-Schmidt Condensation

Sodium acetate catalyzed the multi-component reaction of acetophenone, aromatic aldehydes, and acetoacetanilide in the water-ethanol mixture (1:1) at ambient temperature via Claisen-Schmidt condensation results in the formation of highly substituted cyclohexenones in 89–98% yields. The developed efficient catalytic approach to the substituted cyclohexenones – the promising ...

متن کامل

A highly diastereoselective pinacol coupling reaction of aldehydes and ketones using low-valence niobium generated from Nb(V).

A simple method for the diastereoselective synthesis of racemic 1,2-diol mediated by low-valence niobium generated in situ is described. A 1,4-dioxane-toluene solvent system was found to be essential to achieve higher selectivities and to prevent other reactions of pinacols, such as deoxygenation and acetal formation. Aromatic aldehydes and ketones were converted to the corresponding pinacols w...

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:
  • Molecules

دوره 13 10  شماره 

صفحات  -

تاریخ انتشار 2008