A Stereocontrolled Protocol to Highly Functionalized Fluorinated Scaffolds through a Fluoride Opening of Oxiranes.

نویسندگان

  • Attila Márió Remete
  • Melinda Nonn
  • Santos Fustero
  • Ferenc Fülöp
  • Loránd Kiss
چکیده

A novel selective and substrate-dependent synthetic protocol has been developed towards the synthesis of various fluorine-containing, highly functionalized cycloalkane derivatives. The method involves the stereoselective epoxidation of some unsaturated cyclic β-amino acid derivatives as model compounds, followed by a regioselective fluoride opening of oxiranes under various conditions with Deoxofluor and XtalFluor-E reagents, thereby offering an insight into this new epoxide opening methodology with fluoride.

برای دانلود رایگان 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 highly functionalized fluorinated cispentacin derivatives.

Fluorinated highly functionalized cispentacin derivatives were synthetised starting from an unsaturated bicyclic β-lactam through C=C bond functionalization via the dipolar cycloaddition of a nitrile oxide, isoxazoline opening, and fluorination by OH/F exchange.

متن کامل

A Mild and Green Route for Regio-selective Amination of Oxiranes Using Nanomagnetic Supported Ferrous Ion as a Solid Lewis Acid Catalyst in Water

A mild, green and highly efficient route for regio-selective amination of oxiranes was developed via incorporation of Mn(II), Fe(II), Co(II), Ni(II), Cu(II) and Zn(II) cations onto the surface of hydroxyapatite-encapsulated γ-Fe2O3 nanoparticles (γ-Fe2O3@HAp). Among six magnetically recoverable catalytic systems denoted as [γ-Fe2O3@HAp-MII], the catalyst in which M designated as Fe(II) showed t...

متن کامل

One-pot synthesis of highly regioselective β-azido alcohols catalyzed by Brønsted acidic ionic liquids

In this protocol, 3-(2-carboxybenzoyl)-1-methyl-1H-imidazol-3-ium chloride [Cbmim]Cl and sulfonic acid functionalized pyridinium chloride [pyridine-SO3H]Cl as a new, reusable, and green Brønsted acidic ionic liquid (BAIL) catalyst were synthesized and successfully used for the one-pot ring opening of epoxide with sodium azide (NaN3) in water at room temperature. Epoxides under ring-opening easi...

متن کامل

Synthesis of highly functionalized β-aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines

A rapid and simple procedure was devised for the synthesis of multifunctionalized cyclic β-amino esters and γ-amino alcohols via the 1,3-dipolar cycloaddition of nitrile oxides to β-aminocyclopentenecarboxylates. The opening of the isoxazoline reductive ring to the corresponding highly functionalized 2-aminocyclopentanecarboxylates occurred stereoselectively with good yields.

متن کامل

A Highly Efficient Protocol for the Synthesis of 2-Amidoalkylphenols using SO3H-Functionalized Phthalimide (SFP) under Solvent-free Conditions

A highly efficient and simple protocol for the synthesis of 2-amidoalkylphenols has been described. The one-pot multi-component condensation of phenols with aromatic aldehydes and amides in the presence of catalytic amount of SO3H-functionalized phthalimide (SFP) under solvent-free conditions afford the title compounds in high yields and relatively short reaction times. It is noteworthy that th...

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

عنوان ژورنال:
  • Molecules

دوره 21 11  شماره 

صفحات  -

تاریخ انتشار 2016