Title
Axial chirality inversion at a spiro carbon leads to efficient synthesis of polyimine macrocycle
Author
Mikołaj Zgorzelak, Jakub Grajewski
Year
2020
Journal
Journal of Molecular Structure
Abstract
The synthesis and conformational preferences of a novel chiral macrocyclic polyimine possessing spiro carbon atoms is described. The key feature of the synthesis is the incorporation of an axially chiral surrounding of quaternary carbon atom having four constitutionally identical substituents into the structure of the macrocycle. This is possible by partial hydrolysis, which enables the inversion of absolute configuration, of the spiro-acetal moiety. This approach allows to obtain the macrocyclic product with almost quantitative yield.
Instrument
J-810
Keywords
Circular dichroism, Organic chemistry, Stereochemistry