New C-substituted (1S,4S)-2,5-diazabicyclo[2.2.1]heptane derivatives. Preparation utilizing the directed metalation strategy. Application in enantioselective catalysis

Jordis, Ulrich; Kesselgruber, Martin; Nerdinger, Sven

doi:10.3998/ark.5550190.0002.209

Arkivoc

2001

DOI: 10.3998/ark.5550190.0002.209

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New C-substituted (1S,4S)-2,5-diazabicyclo[2.2.1]heptane derivatives. Preparation utilizing the directed metalation strategy. Application in enantioselective catalysis

Ulrich Jordis¹,

Martin Kesselgruber²,

Sven Nerdinger³

Abstract: New C-substituted derivatives of (1S,4S)-2-methyl-2,5-diazabicyclo[2.2.1]heptane were synthesized utilizing the directed metalation strategy. The absolute configuration of the 3-substituted derivative rests on the comparison of the NMR spectra with a product of proven configurational assignment by X-ray crystallographic analysis.

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Cited by 3 publications

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Synthesis of Novel Derivatives of (1S,4S)‐2,5‐Diazabicyclo[2.2.1]heptane and Their Evaluation as Potential Ligands in Asymmetric Catalysis

et al. 2008

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Thirty-seven (most of them novel) chiral derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane (2-36, 38, 39) were prepared from (S)-trans-4-hydroxyproline. A selection of these chiral ligands were examined as potential ligands in the preparation of catalysts for the enantioselective addition of diethylzinc to aldehydes and as chiral Lewis acid activators in the asymmetric Diels-Alder reaction. In the former system, diamine 30 induced up to 92 % enantiomeric excess in the formation of (S)-phenyl ethyl carbinol, whereas in the case of the cycloaddition reaction between cyclopentadiene and 3-acryloyloxazolidin-2-one the catalytic complex formed

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Synthesis of Novel Derivatives of (1S,4S)‐2,5‐Diazabicyclo[2.2.1]heptane and Their Evaluation as Potential Ligands in Asymmetric Catalysis

et al. 2008

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Octa‐1,7‐diene‐4,5‐diamine Derivatives: Useful Intermediates for the Stereoselective Synthesis of Nitrogen Heterocycles and Ligands for Asymmetric Catalysis

2016

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Synthesis of (1R,4R)-2,5-diazabicyclo[2.2.1]heptane derivatives by an epimerization–lactamization cascade reaction

Cui

et al. 2015

RSC Adv.

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New C-substituted (1S,4S)-2,5-diazabicyclo[2.2.1]heptane derivatives. Preparation utilizing the directed metalation strategy. Application in enantioselective catalysis

Cited by 3 publications

References 6 publications

Synthesis of Novel Derivatives of (1S,4S)‐2,5‐Diazabicyclo[2.2.1]heptane and Their Evaluation as Potential Ligands in Asymmetric Catalysis

Synthesis of Novel Derivatives of (1S,4S)‐2,5‐Diazabicyclo[2.2.1]heptane and Their Evaluation as Potential Ligands in Asymmetric Catalysis

Octa‐1,7‐diene‐4,5‐diamine Derivatives: Useful Intermediates for the Stereoselective Synthesis of Nitrogen Heterocycles and Ligands for Asymmetric Catalysis

Synthesis of (1R,4R)-2,5-diazabicyclo[2.2.1]heptane derivatives by an epimerization–lactamization cascade reaction

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