title: Catalytic enantioselective synthesis of key intermediates for triazole antifungal agents.
abstract: [reaction: see text] A short-step synthesis of versatile chiral building blocks for triazole antifungal agents such as ZD0870 and Sch45450 was developed via catalytic enantioselective cyanosilylation of electron-deficient ketones as the key step. High enantioselectivity was produced using a catalyst prepared from Gd(HMDS)(3) and ligand 5 in a 2:3 ratio. This new catalyst preparation method was superior to the previous method using Gd(O(i)Pr)(3) as a metal source. A rationale for the difference is proposed on the basis of structural studies of the catalyst complexes using ESI-MS.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.
authors.forename: Masato
authors.initials: M
authors.lastname: Suzuki
authors.forename: Nobuki
authors.initials: N
authors.lastname: Kato
authors.forename: Motomu
authors.initials: M
authors.lastname: Kanai
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000935:Antifungal Agents; C508849:Sch45450; D014230:Triazoles; C105015:ZD 0870