Cis-selective double spirocyclization via dearomatization and isom-erization under thermodynamic control

27 July 2022, Version 1
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 meth-ods 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

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