title: Synthesis of (+)-ambrisentan via chiral ketone-catalyzed asymmetric epoxidation.
abstract: The synthesis of optically pure (+)-ambrisentan has been achieved from 3,3-diphenylacrylate in four steps with 53% overall yield and >99% ee at the >100 g scale without column purification. The chiral epoxide intermediate was prepared via asymmetric epoxidation with a fructose-derived diacetate ketone as catalyst.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
authors.forename: Xianyou
authors.initials: X
authors.lastname: Peng
authors.forename: Peijun
authors.initials: P
authors.lastname: Li
authors.forename: Yian
authors.initials: Y
authors.lastname: Shi
mesh_terms: D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010666:Phenylpropionates / Q000138:chemical synthesis* / Q000737:chemistry; D011724:Pyridazines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D007659:Ketones; D010666:Phenylpropionates; D011724:Pyridazines; C467894:ambrisentan