Synthesis of Chiral Pyrrolidinylmethanol Derivatives and Its Catalysis in the Asymmetric Addition of Diethylzinc to Aldehydes

Chem. J. Chinese Universities

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Synthesis of Chiral Pyrrolidinylmethanol Derivatives and Its Catalysis in the Asymmetric Addition of Diethylzinc to Aldehydes

LIU Wen-Min, WANG Ping-An, JIANG Ru, ZHANG Sheng-Yong

Department of Chemistry, School of Pharmacy, the Fourth Military Medical University, Xi'an 710032, China

Received:2005-10-08 Revised:1900-01-01 Online:2006-09-10 Published:2006-09-10
Contact: ZHANG Sheng-Yong

Abstract

Abstract: Chiral β-amino alcohols, using L-proline as raw material, were synthesized by esterization, protection of amino-group, Grignard reaction and catalytic hydrogenolysis. They were used as chiral catalysts in the asymmetric addition of diethylzinc to aldehydes. The effects of the amount structure of and the catalysts, solvent and reaction temperature on enantioselectivity were also studied. When the molar fraction of catalyst 5% was relative to aldehyde was used, with toluene as solvent at -10 ℃, (S)-N-benzyl-2-(di-α-naphthylhydroxymethyl)pyrrolidine(3) was successfully applied to the catalytic enantioselective addition of diethylzinc to aldehydes to give secalcohols in a good to high yields up to 82% enantiomeric excesses.

Key words: L-Proline, Asymmetric addition, Chiral β-aminoalcohols, Catalysis, Diethylzinc

CLC Number:

O621

TrendMD:

LIU Wen-Min, WANG Ping-An, JIANG Ru, ZHANG Sheng-Yong. Synthesis of Chiral Pyrrolidinylmethanol Derivatives and Its Catalysis in the Asymmetric Addition of Diethylzinc to Aldehydes[J]. Chem. J. Chinese Universities, doi: .

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Synthesis of Chiral Pyrrolidinylmethanol Derivatives and Its Catalysis in the Asymmetric Addition of Diethylzinc to Aldehydes

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