Structural Diversity-Oriented Synthesis of Orthogonally Protected Cyclic Amino Acid Derivatives with Multiple Stereogenic Centers

Nonn, Melinda and Remete, Attila M. and Kiss, Loránd (2020) Structural Diversity-Oriented Synthesis of Orthogonally Protected Cyclic Amino Acid Derivatives with Multiple Stereogenic Centers. Helvetica Chimica Acta, 103 (7). pp. 1-7. ISSN 1522-2675

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Abstract

The synthesis of three-dimensional cyclopentane amino acid derivatives with multiple stereocenters and with high regiochemical and diastereochemical diversity has been achieved starting from cyclopentadiene-derived β-aminocyclopentenecarboxylic acid. The small-molecular design was based on stereo- and regiocontrolled functionalization of the starting cyclopentene β-amino acid through stereoselective oxirane formation/regioselective oxirane opening and resulted in regio-and diastereoisomers of novel orthogonally protected aminocyclopentanecarboxylates.

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