Events The 4th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

10.3390/ecsoc-4-01901

This submission belongs to the session c. Bioorganic Chemistry and Natural Products of the event The 4th International Electronic Conference on Synthetic Organic Chemistry

Published date

11 Sep, 2000

Citation

U. Kazmaier, H. Mues, Via Ester Enolate Claisen Rearrangements To a Variety of Non-Proteinogenic Amino Acids, in Proceedings of The 4th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2000, MDPI: Basel, Switzerland, 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 ¹

U. Kazmaier ¹

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

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.

Keywords

n/a

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