Ferrocene-Based Chiral Phosphine-Triazines: A New Family of Highly Efficient P,N Ligands for Asymmetric Catalysis

نویسندگان

  • Xiang-Ping Hu
  • Hui-Lin Chen
  • Zhuo Zheng
چکیده

The presence of the additional heterocyclic nitrogen atoms in chiral P,N ligands has an important influence on the asymmetric catalysis, and a clear trend was observed in the present research that the enantioselectivity and reactivity were significantly increased by raising the number of heterocyclic nitrogen atoms in these P,N ligands. Through finely tuning the number of heterocyclic nitrogen atoms, a new family of ferrocene-based chiral phosphine-triazine ligands with three heterocyclic nitrogen atoms has been developed and successfully applied in Pd-catalyzed asymmetric allylic substitution. Up to 99% ee with 99% yield of allylic alkylation products and 94% ee of allylic amination products have been obtained by the use of ligand (Rc,Sp)-1f with a 4,6-diphenoxy1,3,5-triazine moiety.

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 and highly stereoselective synthesis of new P-chiral 1,5-diphosphanylferrocene ligands and their use in enantioselective hydrogenation.

An efficient and highly stereoselective synthesis of P-chiral 1,5-diphosphanylferrocene ligands has been developed, and the introduction of P-chirality in ferrocene-based phosphine ligands enhances the enantioselective discrimination produced by the corresponding catalyst when matching of the planar chirality, the chirality at carbon and the chirality at phosphorus occurs.

متن کامل

Synthesis of ferrocene-based amido-phosphine ligands via highly diastereoselective ortho-lithiation and their application in Pd-catalyzed asymmetric allylic alkylations

An efficient synthesis of novel planar chiral ferrocene-based amido-phosphine ligands was accomplished via highly diastereoselective ortho-lithiation and subsequent in situ trapping with chlorodiphenylphosphine. The palladium complexes of mono-phosphino ferrocenecarboxamide, bis-phosphino ferrocenedicarboxamide ligands, and analogues with a ferrocenophane framework were applied in the allylic a...

متن کامل

Ferrocene phosphane-heteroatom/carbon bidentate ligands in asymmetric catalysis.

Chiral ferrocene derivatives belong to privileged ligand classes for asymmetric transition metal catalysed reactions. Hetero-bidentate phosphane ligands are hybrid ligands, which combine the properties of phosphorus with those of other donor atoms. This feature creates further asymmetry around the metal centre, which may be helpful for increasing the stereoinduction. Therefore, hetero-bidentate...

متن کامل

Ion-paired chiral ligands for asymmetric palladium catalysis.

Conventional chiral ligands rely on the use of a covalently constructed, single chiral molecule embedded with coordinative functional groups. Here, we report a new strategy for the design of a chiral ligand for asymmetric transition-metal catalysis; our approach is based on the development of an achiral cationic ammonium-phosphine hybrid ligand paired with a chiral binaphtholate anion. This ion...

متن کامل

Chiral ferrocene-based phosphine-imine and sulfur-imine ligands for palladium-catalyzed asymmetric allylic alkylation of cycloalkenyl esters

Chiral ferrocene-based phosphine-imine ligands 1–3 and sulfur-imine ligand 4 were applied in the palladium-catalyzed asymmetric allylic alkylation of cycloalkenyl esters. The results revealed that the substitutents in aryl ring, ferrocenylmethyl and benzyliene position strongly affected the enantioselective induction of phosphine-imine ligands, and the most stereoselective ligand was ferrocenyl...

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:

دوره   شماره 

صفحات  -

تاریخ انتشار 2005