title: Catalytic asymmetric aminohydroxylation with amino-substituted heterocycles as nitrogen sources.
abstract: The suprafacial, vicinal addition of a heterocyclic moiety and a hydroxyl group is achieved by the osmium-catalyzed asymmetric aminohydroxylation (AA) of olefins with amino-substituted heterocycles as the nitrogen sources. Amino alcohols are obtained in up to 97 % yield and with up to 99 % ee when a ligand derived from dihydroquinidine (DHQD-L) is used [Eq. (1); R(i) indicates the remaining portion of the heterocycle (Het); H2 O is the O source]. The AA can now be considered as a means to directly introduce complex, biologically relevant substructures to hydrocarbon backbones.
authors.affiliation: Department of Chemistry (and) The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-784-7562.
authors.forename: L J
authors.initials: LJ
authors.lastname: Goossen
authors.forename: H
authors.initials: H
authors.lastname: Liu
authors.forename: K R
authors.initials: KR
authors.lastname: Dress
authors.forename: K B
authors.initials: KB
authors.lastname: Sharpless
keywords: Amino alcohols; Aminohydroxylations; Asymmetric synthesis; Heterocycles; Homogeneous catalysis