Synthesis of New Chiral Diphosphine-borane Complex and Its Application to the Catalytic Asymmetric Hydrogenation

Abstract

Abstract: The high enantiomeric pure phenylglycol was synthesized from styrene by Sharpless asymmetric dihydroxylation. The diol was converted to chiral diphosphine-borane complex by esterification and nucleophilic substitution respectively. The complex was superior to free phosphine ligands which are sensitive to atmosphere. It's easy to prepare, purify and reserve. The complex was decomplexated in the presence of HBF₄·OMe₂ to yield quantitatively the free diphosphine which reacted directly with [Rh(COD)Cl]₂ forming in situ catalyst. The asymmetric hydrogenation of methyl z-α-acetamidocinnamate has been accomplished in the presence of catalyst in 100% chemical conversion and 88% e.e..

Key words: Chiral diphosphine borane complex, Asymmetric dihydroxylation, Asymmetric hydrogenation, Asymmetric synthesis

CLC Number:

O621.3⁺4

TrendMD:

JIANG Ru, NAN Peng-Juan, LIU Wei, LI Xiao-Ye, ZHANG Sheng-Yong . Synthesis of New Chiral Diphosphine-borane Complex and Its Application to the Catalytic Asymmetric Hydrogenation[J]. Chem. J. Chinese Universities, 2001, 22(6): 936.

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Synthesis of New Chiral Diphosphine-borane Complex and Its Application to the Catalytic Asymmetric Hydrogenation

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