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Structural Diversity‐Oriented Synthesis of Orthogonally Protected Cyclic Amino Acid Derivatives with Multiple Stereogenic Centers
Author(s) -
n Melinda,
Remete Attila M.,
Kiss Loránd
Publication year - 2020
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.202000090
Subject(s) - chemistry , stereocenter , regioselectivity , cyclopentene , stereoselectivity , cyclopentadiene , cyclopentane , diastereomer , stereochemistry , amino acid , enantioselective synthesis , organic chemistry , catalysis , biochemistry
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.