Synthesis of 1,4-Bis(9-O-quininyl)phthalazine and Its Application as a Ligand to the Catalytic Asymmetric Dihydroxylation of Olefins

Chem. J. Chinese Universities ›› 2003, Vol. 24 ›› Issue (7): 1216.

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Synthesis of 1,4-Bis(9-O-quininyl)phthalazine and Its Application as a Ligand to the Catalytic Asymmetric Dihydroxylation of Olefins

SUN Xiao-Li, KUANG Yong-Qing, NAN Peng-Juan, ZHANG Sheng-Yong

The Teaching and Research Section of Chemistry, the 4th Military Medical University, Xi′an 710032, China

Received:2002-07-02 Online:2003-07-24 Published:2003-07-24

Abstract

Abstract:

An improved procedure for the preparation of 1,4-bis(9-O-quininyl) phthalazine[(QN)₂PHAL] and the rudimentary application of (QN)₂PHAL to the catalytic asymmetric dihydroxylation of olefins were described. (QN)₂PHAL was synthesized in a good yield by the reaction of quinine with 1,4-dichlorophthalazine in the presence of K₂CO₃ and KOH in refluxing toluene. The asymmetric dihydroxylation of four olefins with (QN)₂PHAL as the chiral ligand showed an excellent enantioselectivity and activity.

Key words: 1,4-Bis(9-O-quininyl)phthalazine, Asymmetric dihydroxylation, Chiral vicinal diol

CLC Number:

O621

TrendMD:

SUN Xiao-Li, KUANG Yong-Qing, NAN Peng-Juan, ZHANG Sheng-Yong . Synthesis of 1,4-Bis(9-O-quininyl)phthalazine and Its Application as a Ligand to the Catalytic Asymmetric Dihydroxylation of Olefins[J]. Chem. J. Chinese Universities, 2003, 24(7): 1216.

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Synthesis of 1,4-Bis(9-O-quininyl)phthalazine and Its Application as a Ligand to the Catalytic Asymmetric Dihydroxylation of Olefins

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