title: The influence of exocyclic stereochemistry on the tethered aminohydroxylation reaction.
abstract: A new strategy that employs an exocyclic stereocenter to effect diastereocontrol in the tethered aminohydroxylation (TA) reaction is applied to the stereoselective synthesis of a range of amino alcohols in good to excellent yields, and with anti selectivities of up to 20:1. The influence of the reaction conditions and substrate parameters on the level of diastereocontrol is described. Furthermore, an "inside alkoxy" model is employed to rationalize the sense and degree of stereoselectivity observed in these systems.
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Donohoe
authors.forename: Adam R
authors.initials: AR
authors.lastname: Lacy
authors.forename: Akshat H
authors.initials: AH
authors.lastname: Rathi
authors.forename: Daryl S
authors.initials: DS
authors.lastname: Walter
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry; D006900:Hydroxylation; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000588:Amines; D000605:Amino Alcohols; D006571:Heterocyclic Compounds