Enantiomerically pure bicyclo[3.3.1]nona-2,6-diene as the sole source of enantioselectivity in BIPHEP-Rh asymmetric hydrogenation.

نویسندگان

  • Tharmalingam Punniyamurthy
  • Monika Mayr
  • Alexander S Dorofeev
  • Carole J R Bataille
  • Silvia Gosiewska
  • Bao Nguyen
  • Andrew R Cowley
  • John M Brown
چکیده

In situ resolution of the rapidly racemising diphosphine BIPHEP and its relatives with the cationic Rh complex of (S,S)-bicyclonona-2,6-diene permits the asymmetric hydrogenation of dehydroamino esters.

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

Homoconjugation vs. exciton coupling in chiral α,β-unsaturated bicyclo[3.3.1]nonane dinitrile and carboxylic acids.

The chiroptical properties of enantiomerically pure bicyclo[3.3.1]nona-2,6-diene-2,6-dicarbonitrile and related acids were studied by circular dichroism spectroscopy and theoretical computations. A consideration of the molecular structure of the synthesized difunctional compounds revealed that chromophores are predisposed to transannular through-space interaction due to a favourable conformatio...

متن کامل

Asymmetric Rh-Catalyzed Hydrogenation of Enamides with a Chiral 1,4-Bisphosphine Bearing Diphenylphosphino Groups

Much effort has been devoted to the development of efficient asymmetric synthetic methods for the preparation of enantiomerically enriched compounds.1,2 Among various methods for the enantiomerically selective synthesis of chiral organic compounds from prochiral precursors, enantioselective catalytic hydrogenation of dehydro precursors has been extensively developed.3 In fact, asymmetric hydrog...

متن کامل

Monodentate chiral spiro phosphoramidites: efficient ligands for rhodium-catalyzed enantioselective hydrogenation of enamides.

Optically active -arylalkylamines are an important class of compounds that are widely used in organic and pharmaceutical synthesis, and much effort has been made to develop efficient asymmetric synthetic methods for them.[1] Asymmetric catalytic hydrogenation of enamides, initiated by Kagan et al. ,[2] provides a direct and convenient route to chiral amine derivatives. However, many well-known ...

متن کامل

Synthesis of ortho-phenyl substituted MeO-BIPHEP ligand and its application in Rh-catalyzed asymmetric hydrogenation

A new BIPHEP-type ligand with phenyl groups at the 3,30-positions, o-Ph-MeO-BIPHEP 3 was prepared. This ligand afforded excellent enantioselectivities when used in the Rh-catalyzed asymmetric hydrogenation of a-dehydroamino acid derivatives. The strong influence of o-phenyl groups of the ligand on the enantioselectivities of the reaction has been demonstrated by a comparison with its parent lig...

متن کامل

Highly enantioselective asymmetric hydrogenation of alpha-phthalimide ketone: an efficient entry to enantiomerically pure amino alcohols.

A new type of alpha-phthalimide ketones was hydrogenated in excellent enantioselectivity by using a Ru-(C3-TunePhos) complex as the catalyst. Up to 10 000 turnovers have been achieved in more than 99% ee in the hydrogenation reaction. A dynamic kinetic resolution study for the synthesis of threonine was performed, and high anti selectivity (>97:3) was observed for the first time. An efficient m...

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

عنوان ژورنال:
  • Chemical communications

دوره 41  شماره 

صفحات  -

تاریخ انتشار 2008