Control of stereogenic oxygen in a helically chiral oxonium ion.

ABSTRACT: The control of tetrahedral carbon stereocentres remains a focus of modern synthetic chemistry and is enabled by their configurational stability. By contrast, trisubstituted nitrogen¹, phosphorus² and sulfur compounds³ undergo pyramidal inversion, a fundamental and well-recognized stereochemical phenomenon that is widely exploited⁴. However, the stereochemistry of oxonium ions-compounds bearing three substituents on a positively charged oxygen atom-is poorly developed and there are few applications of oxonium ions in synthesis beyond their existence as reactive intermediates^5,6. There are no examples of configurationally stable oxonium ions in which the oxygen atom is the sole stereogenic centre, probably owing to the low barrier to oxy

SUBMITTER: Smith O 

PROVIDER: S-EPMC10017494 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature