Via Ester Enolate Claisen Rearrangements
To a Variety of Non-Proteinogenic Amino Acids

H. Mues; U. Kazmaier

doi:10.3390/ecsoc-4-01901

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Via Ester Enolate Claisen Rearrangements To a Variety of Non-Proteinogenic Amino Acids

H. Mues

U. Kazmaier

¹ University of Heidelberg, Department of Chemistry, Im Neuenheimer Feld 270, D- 69120 Heidelberg, Germany

Published: 11 September 2000 by MDPI in The 4th International Electronic Conference on Synthetic Organic Chemistry session Bioorganic Chemistry and Natural Products

https://doi.org/10.3390/ecsoc-4-01901

Abstract: Allylic esters of TFA-protected amino acids undergo asymmetric Claisen rearrangements in the presence of cinchona alkaloids, giving rise to g,d-unsaturated amino acids in a highly stereoselective fashion. The products are useful precursors for the short and efficient synthesis of more complex compounds such as substituted 4-hydroxyprolines, 4-hydroxyornithines and iminosugars.

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H. Mues

U. Kazmaier