Stereo- and regiocontrolled synthesis of highly functionalized cyclopentanes with multiple chiral centers

Nonn, Melinda and Binder, Adrienn and Volk, Balázs and Kiss, Loránd (2020) Stereo- and regiocontrolled synthesis of highly functionalized cyclopentanes with multiple chiral centers. SYNTHETIC COMMUNICATIONS, 50 (8). pp. 1199-1209. ISSN 0039-7911 (print); 1532-2432 (online)

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Abstract

The synthesis of some highly substituted three-dimensional cyclopentanes with multiple chiral centers and with high regiochemical and stereochemical diversity has been accomplished starting from cyclopentadiene-derived aminocyclopentenecarboxylic acids. The small-molecular design consisted of stereo- and regiocontrolled functionalization of the starting cyclopentene b- and c-amino acids through oxirane formation/oxirane opening and afforded regio- and diastereoisomers of orthogonally protected aminocyclopentanecarboxylates.

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