Conformationally Restricted Carbocyclic γ-Amino Acids: Synthesis of Diastereomeric 3-Amino-5-arylcyclopentane 1-Carboxylic Acids Stephen Hanessian, Adrien Dumas, Da Li, Steven Bonert, Prashansing Aubeelucksing, and Arnaud-Pierre Schaffner Georg Thieme Verlag KG AbstractA Trost Pd-catalyzed [3+2] cycloaddition between a p-benzyloxy cinnamate bearing an Evans auxiliary and 1-trimethylsilyl-2-acetoxymethylpropene is disclosed leading to, after functional group manipulation, previously unreported diastereoisomeric 3-amino-5-arylcyclopentane 1-carboxylic acids via the corresponding 3-hydroxy and 3-azido precursors. The availability of these conformationally restricted cyclic amino acids may find utility in the context of CNS-active compounds related to GABA, or as peripheral units of bioactive pharmaceuticals. An expedient alternative 4-step synthesis of 3S-amino-5S-p-hydroxyphenyl-1S-cyclopentane carboxylic acid methyl ester was achieved starting with the (–)-Vince lactam and utilizing a regio- and diastereoselective Pd-catalyzed hydroarylation reaction.
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Conformationally Restricted Carbocyclic γ-Amino Acids: Synthesis of Diastereomeric 3-Amino-5-arylcyclopentane 1-Carboxylic Acids A Dumas, D Li, S Bonert, P Aubeelucksing, AP Schaffner, S Hanessian Synthesis 2023
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Conformationally Restricted Carbocyclic γ-Amino Acids: Synthesis of Diastereomeric 3-Amino-5-arylcyclopentane 1-Carboxylic Acids A Dumas, D Li, S Bonert, P Aubeelucksing, AP Schaffner, S Hanessian Synthesis 2023 Citations: 1