Asymmetric homogeneous hydrogenation of 2,5-disubstituted furans.

نویسندگان

  • Petra Feiertag
  • Martin Albert
  • Ulrike Nettekoven
  • Felix Spindler
چکیده

A homogeneous catalyst system for the asymmetric cis-hydrogenation of 2,5-disubstituted furans leading to 2',3'-dideoxynucleoside analogues is described. Best enantioselectivities (ee values of up to 72%) were obtained with cationic rhodium complexes ligated by diphospholanes of the butiphane family. The selectivity of the hydrogenation was reversed by the addition of a base or a polar protic solvent in certain cases. Ferrocene- and proline-based systems gave significant, but lower, ee values.

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

Asymmetric hydrogenation of disubstituted furans.

An enantioselective hydrogenation of disubstituted furans has been developed by using a chiral ruthenium catalyst with N-heterocyclic carbene ligands. This reaction converts furans into valuable enantioenriched disubstituted tetrahydrofurans.

متن کامل

Asymmetric hydrogenation of furans and benzofurans with iridium-pyridine-phosphinite catalysts.

Enantioselective hydrogenation of furans and benzofurans remains a challenging task. We report the hydrogenation of 2- and 3-substituted furans by using iridium catalysts that bear bicyclic pyridine-phosphinite ligands. Excellent enantioselectivities and high conversions were obtained for monosubstituted furans with a 3-alkyl or 3-aryl group. Furans substituted at the 2-position and 2,4-disubst...

متن کامل

Pd-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols via capture of active tautomers.

An efficient palladium-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols has been developed via capture of the active tautomers. A wide variety of 2,5-disubstituted and 2,4,5-trisubstituted pyrazolidinones have been synthesized with up to 96% and 95% ee, respectively. The hydrogenation pathway includes Brønsted acid promoted tautomerization of pyrazol-5-ols and Pd-catalyz...

متن کامل

Organocatalytic enantioselective reduction of pyridines.

Asymmetric hydrogenation is one of the most important enantioselective reactions. Although the hydrogenation, transfer hydrogenation, and hydrosilylation of various substrates in the presence of metal catalysts have been described, the asymmetric reduction of aromatic and heteroaromatic compounds still represents a great challenge. This situation is particularly true for the enantioselective hy...

متن کامل

The Gas - Phase Conversion of Bio - Derived 5 - Methylfurfural to 2 , 5 - Dimethylfuran

* The Gas-Phase Conversion of Bio-Derived 5-Methylfurfural to 2,5-Dimethylfuran Aaron Oberg and Dennis Miller *Concern over global warming and limited oil reserves has resulted in an increased interest in the production of fuels and chemicals from biomass. Currently there is considerable interest in a class of bio-derived molecules referred to as furans. Furans contain an aromatic heterocyclic ...

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:
  • Organic letters

دوره 8 18  شماره 

صفحات  -

تاریخ انتشار 2006