Cis-selective double spirocyclization via dearomatization and isomerization under thermodynamic control

15 September 2022, Version 3
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Spiro compounds have been considered key scaffolds for pharmaceutical applications. Although many synthetic methods exist for monospirocycles, fewer approaches are known for dispirocycles. Here, we report a highly cis-selective method for constructing a 5/6/5-dispirocyclic structure containing pyrrolidine and γ-lactam rings with various substit-uents from a series of N-arylpropiolamides. The high cis-selectivity would result from isomerization under thermody-namic control. Cis- and trans-diastereomers can be in equilibrium, favoring cis-adducts.

Keywords

dispirocycle
dearomatization
spirocyclization
equilibrium

Supplementary materials

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Description
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Supporting Information
Description
Result of control experiments Result of calculation of the relative energies NMR spectra of synthetic compounds
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