Stereochemical Aspects—Conformation and Configuration

Berg, Ulf

doi:10.1002/9780470682531.pat0317

Cited by 1 publication

(1 citation statement)

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“…The increasingly important role of the cyclobutane framework for pharmaceutical and medicinal chemistry , is closely related to its structural features. The nonplanarity and sp 3 -enrichment, − relatively rigid structure, and stereochemical aspects associated with introduction of a cyclobutane core into the parent molecules endow them with unique biological characteristics while largely retaining the chemical properties. Such modifications allow fine-tuning of the pharmacological profile of lead compounds and drug candidates, providing advantages on potency, selectivity, stability, safety, etc .…”

Section: Introductionmentioning

confidence: 99%

Expanding the Chemical Space of 1,2-Difunctionalized Cyclobutanes

et al. 2023

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An efficient approach to the synthesis of previously unavailable or hardly accessible 1,2-difunctionalized cyclobutanes (mostly with NH 2 /NHBoc, OH, SH, or SO 2 F groups attached to the carbocycle either directly or via a CH 2 unit) relying on the divergent strategy is described. This class of compounds provides sp 3 -enriched and conformationally restricted building blocks that are of special demand for medicinal chemistry. The target compounds were prepared not only as pure racemic (±)-cis-and (±)-trans-diastereomers but in some cases also as single enantiomers. The developed procedures are readily scaled up and allow obtaining the target compounds on an up to hundred-gram scale. On the basis of the results of 20 X-ray diffraction experiments, structural characterization of the 1,2-difunctionalized cyclobutane core was performed using the extended Cremer−Pople puckering parameters and exit vector (EVP) plots.

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