Ontology highlight
ABSTRACT:
SUBMITTER: Bracegirdle A
PROVIDER: S-EPMC2633665 | biostudies-literature | 2008
REPOSITORIES: biostudies-literature
Beilstein journal of organic chemistry 20081204
Atropisomeric biaryl aldehydes undergo diastereoselective condensation with (-)-ephedrine and with a proline-derived diamine, with selectivity highly dependent on solvent, temperature and reaction conditions. Levels of thermodynamic control up to 5:1 may be obtained by heating the diamine with the aldehyde in a sealed tube. Alternatively, crystallisation-induced dynamic transformation allows isolation of a single diastereoisomer in up to 85% yield. Hydrolysis and reduction of the major diastereo ...[more]