Diastereoselective Addition of Organolithium to Ferrocene-Carboxaldehyde Imines Derived from (R)- and (S)-1-Phenylethylamine: The Effect of External Additives

Hui-Qing      Zhang; Zhi-Ming      Zhou; Min      Fang

doi:10.2174/157017806779117085

Abstract

An efficient and flexible asymmetric synthesis of chiral ferrocenylamines 3a-c via diastereoselective addition of organolithium compounds to chiral imines is described. High diastereoselectivity(93% de) was observed with ferrocenecarboxaldehyde imine 2b in the presence of the Lewis acids BF3oOEt2.

Keywords: Ferrocene, optically active amines, ferrocenecarboxaldehyde imine, asymmetric addition, organolithium, compounds, chiral synthesis

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Letters in Organic Chemistry

Title: Diastereoselective Addition of Organolithium to Ferrocene-Carboxaldehyde Imines Derived from (R)- and (S)-1-Phenylethylamine: The Effect of External Additives

Volume: 3 Issue: 11

Author(s): Hui-Qing Zhang, Zhi-Ming Zhou and Min Fang

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Keywords: Ferrocene, optically active amines, ferrocenecarboxaldehyde imine, asymmetric addition, organolithium, compounds, chiral synthesis

Abstract: An efficient and flexible asymmetric synthesis of chiral ferrocenylamines 3a-c via diastereoselective addition of organolithium compounds to chiral imines is described. High diastereoselectivity(93% de) was observed with ferrocenecarboxaldehyde imine 2b in the presence of the Lewis acids BF3oOEt2.

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Zhang Hui-Qing, Zhou Zhi-Ming and Fang Min, Diastereoselective Addition of Organolithium to Ferrocene-Carboxaldehyde Imines Derived from (R)- and (S)-1-Phenylethylamine: The Effect of External Additives, Letters in Organic Chemistry 2006; 3 (11) . https://dx.doi.org/10.2174/157017806779117085