title: An alternative stereoselective synthesis of (R)- and (S)-Rosaphen® via asymmetric catalytic hydrogenation.
abstract: We report an alternative synthesis of the two enantiomers of the floral fragrance Rosaphen®. The key intermediate 2-methyl-5-phenylpentanoic acid 3 is synthesized via asymmetric hydrogenation (ee up to 99%) in the presence of an in situ prepared ruthenium catalyst containing the chiral ferrocenyl phosphine Mandyphos-4.
authors.affiliation: Dipartimento di Scienze Molecolari e Nanosistemi, Università Cà Foscari di Venezia, Dorsoduro 2137, 30123 Venezia, Italy.
authors.forename: Ugo
authors.initials: U
authors.lastname: Matteoli
authors.forename: Valentina
authors.initials: V
authors.lastname: Beghetto
authors.forename: Alberto
authors.initials: A
authors.lastname: Scrivanti
authors.forename: Manuela
authors.initials: M
authors.lastname: Aversa
authors.forename: Matteo
authors.initials: M
authors.lastname: Bertoldini
authors.forename: Sara
authors.initials: S
authors.lastname: Bovo
mesh_terms: D002384:Catalysis; D006865:Hydrogenation; D008968:Molecular Conformation; D015394:Molecular Structure; D000439:Pentanols / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C570213:2-methyl-5-phenylpentanol; D000439:Pentanols; D010720:Phosphines; D012428:Ruthenium