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. 2025 Sep 5;27(35):9669-9673.
doi: 10.1021/acs.orglett.5c02839. Epub 2025 Aug 26.

Rotational Motion in Bispidines: A Conformational Study

Francesco Migliano  1 , Luca Pozzi  1 , Andrea Citarella  1 , Giovanni Macetti  1 , Leonardo Lo Presti  1 , Daniele Passarella  1 , Valerio Fasano  1
Affiliations

Rotational Motion in Bispidines: A Conformational Study

Francesco Migliano et al. Org Lett. .

Abstract

A detailed conformational analysis of N-substituted bispidines has been performed to determine the factors governing the restricted rotational motion induced by the substituents. This investigation combines computational studies of the transition state involved in the rotation with experimental characterization of the rotamers arising from the restricted rotation.

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Figures

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1. A) Examples of Natural and Synthetic Relevant Bispidines; B) Planar Chirality in Diacyl Bispidine; C) Conformational Study of Rotameric Bispidines (This Work)
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2. Computed Conformational Analysis for the Inversion of Planar Chirality in Ac-H and Ac-Me (H Other than N′-H Omitted for Clarity)
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3. A) Computed Conformational Analysis for the Inversion of Planar Chirality in Boc-R′; B) Zoom of 1H NMR Spectra (CDCl3, 298 K) of Boc-H and Boc-Cl; C) COSY Spectrum (CDCl3, 298 K) of Boc-Cl (the Green and Purple Circles Show the 4JH–H Long-Range Couplings)
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4. A) Inversion of Planar Chirality in Boc-PEA; B) Zoom of 1H NMR Spectra in DMSO-d 6 below and above the Coalescence Temperature
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5. Zoom of the 1H NMR Spectra (CDCl3, 298 K) of N-Nitrosamines NO-Bn (A) and Tropane Derivatives 6 and 7 (B)
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6. Summary of Carbonyl Bispidines Analyses
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