Novel chiral phosphite ligands with stable properties, mild reaction conditions, high catalytic yields and enantioselectivity.

Chirality is closely related to life phenomena and significantly affects material properties. Our demand for optically active substances has led to rapid progress in the research and development of chiral compounds.

Dr. Lailai Wang has developed a series of novel chiral phosphite ligands. These Novel and Efficient Chiral Phosphite Ligands can be complexed with transition metals to prepare chiral catalysts, which are successfully applied to asymmetric hydrogenation, hydroformylation, allylic alkylation and 1,4-conjugate addition.

Advantages

  • White solid, stable to water and air, and easy to store.
  • High catalytic yields and enantioselectivity, up to 95% (Fig.1 and 2).
  • Mild reaction conditions, easy to operate.

 

Applications

  • Copper chiral complexes were prepared by using L-tartaric acid-derived phosphite ligands and applied to the 1,4-conjugate addition of organozinc reagents to 2-cyclopentenone and 2-cyclohexenone, both achieving up to 95% enantioselectivity[1] (Fig.1).

    Fig.1 Application of L-tartrate-type chiral phosphite ligands to the asymmetric 1,4-conjugate addition of cyclic ketene, achieving up to 99% yield and 95% enantioselectivity[1]
  • Rhodium chiral complexes prepared in situ by using glucoside ligands can obtain up to 98% enantioselectivity in asymmetric hydrogenation with functionalized olefins as substrates under mild conditions [2] (Fig.2).

    Fig.2 Application of glucoside chiral phosphite ligands to asymmetric hydrogenation of functionalized olefins, obtaining up to 99% yield and 98% enantioselectivity[2]

Reference:

  1. Ai-ping Xing, Cui-bing Bai, Lai-lai Wang. Tetrahedron, 2013, 69, 455-459.
  2. Qing-Lu Zhao, Xiao Miao, Lai-Lai Wang. Tetrahedron: Asymmetry, 2013, 24, 104-107.

1,2:5,6-Di-O-isopropylidene-3,4-bis[(R)-1,1'-H8-binaphthyl-2,2'-diyl]phosphite-D-mannitol
1810982

1,2:5,6-Di-O-isopropylidene-3,4-bis[(R)-1,1'-binaphthyl-2,2'-diyl]phosphite-D-mannitol
1810983

2,4-Bis{[(S)-1,1'-H8-binaphthyl-2,2'-diyl]phosphite}-methyl 3,6-anhydro-α-D-glucopyranoside
1810985

Dr. Wang’s Profile

He is a researcher and PhD supervisor at Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences. His principle research interest lies in the synthesis and application of chiral ligands.

By shuhan yang

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