Taniaphos was first formally reported by Prof. Paul Knochel’s research team from Germany in 1999. The name “Tania” originates from a member of the research group. Breaking the conventional design logic of C₂-symmetric phosphine ligands, the team pioneered the 1,5-diphosphino ferrocene scaffold, constructing a unique chiral cavity with balanced rigidity and flexibility.

Built on a ferrocene core, it features a distinctive 1,5-bisphosphine structure. Upon coordination with metals, it forms a stable eight-membered chelate ring with flexible conformation and outstanding coordination capacity.

Various substituents including methyl, pyrrolidinyl, isopropyl, amino groups and more can be readily introduced at the benzylic position, enabling rapid derivatization and customizable structural tuning.

It simultaneously possesses ferrocene planar chirality and side-chain central chirality, allowing precise modulation of the steric environment and delivering exceptional chiral induction performance.

As a classic ferrocene-based chiral bisphosphine ligand, Taniaphos efficiently coordinates with transition metals such as Ru, Rh, Cu and Ag. Benefiting from its exclusive chiral cavity and spatial configuration, it achieves outstanding enantioselective transformations of C=C, C=O and C=N unsaturated bonds in classic reactions including asymmetric hydrogenation, conjugate addition and cycloaddition. Taking Taniaphos (CAS: 255884-98-1) as an example, its main applications are outlined below:

This is the flagship application of Taniaphos, compatible with Ru and Rh catalytic systems for highly enantioselective chiral hydrogenation of diverse carbonyl and carbon-carbon double bonds.

Taniaphos exhibits excellent compatibility with Cu(I) catalytic systems, delivering unique chiral induction and stereocontrol in conjugate addition and Mannich-type reactions, and serves as the optimal ligand in numerous research works.

Combined with Cu catalyst, Taniaphos enables the 1,6-conjugate addition of Grignard reagents to in-situ generated aza-p-quinone methides, solving the synthetic challenge of chiral 4-secondary alkyl anilines and offering an efficient synthetic route for this class of pharmaceutical intermediates.

Taniaphos acts as a uniquely advantageous ligand. Under Cu(I) catalysis, it facilitates highly regioselective and enantioselective transformations, playing an irreplaceable role in constructing remote chiral centers.

Taniaphos is the top-performing chiral ligand for Cu(I)-catalyzed asymmetric α-addition between ketimines and aldimines, enabling efficient synthesis of high-value chiral anti-1,2-diamine building blocks.

Anhui Kaitailai Platinum supplies a full series of Taniaphos ligands and provides custom synthesis services. We welcome global researchers and enterprises for inquiries and cooperation.

[1] T. Ireland, G. Grossheimann, C. Wieser-Jeunesse, P. Knochel. Ferrocenyl Ligands with Two Phosphanyl Substituents in the α,ε positions for the Transition Metal Catalyzed Asymmetric Hydrogenation of Functionalized Double Bonds. Angew. Chem. Int. Ed., 1999, 38, 3212.[2] K. Tappe, P. Knochel. New efficient synthesis of Taniaphos ligands: application in ruthenium- and rhodium-catalyzed enantioselective hydrogenations. Tetrahedron Asymmetry, 2004, 15, 91.[3] M. Zurro, L. Ge, S. R. Harutyunyan. Catalytic Access to 4‑(sec-Alkyl)Anilines via 1,6-Conjugate Addition of Grignard Reagents to in Situ Generated aza‑p‑Quinone Methides. Org. Lett., 2022, 24, 6686.[4] H.-J. Zhang, C.-Y. Shi, F. Zhong, L. Yin. Direct Asymmetric Vinylogous and Bisvinylogous Mannich-Type Reaction Catalyzed by a Copper(I) Complex. J. Am. Chem. Soc., 2017, 139, 2196.[5] X.-C. Gan, C.-Y. Zhang, F. Zhong, P. Tian, L. Yin. Synthesis of chiral anti-1,2-diamine derivatives through copper(I)-catalyzed asymmetric α-addition of ketimines to aldimines. Nat. Commun., 2020, 11, 4473.