title: Tungsten-catalyzed regio- and enantioselective aminolysis of trans-2,3-epoxy alcohols: an entry to virtually enantiopure amino alcohols.
abstract: The first catalytic enantioselective aminolysis of trans-2,3-epoxy alcohols has been accomplished. This stereospecific ring-opening process was efficiently promoted by a tungsten/bis(hydroxamic acid) catalytic system, furnishing various anti-3-amino-1,2-diols with excellent regiocontrol and high enantioselectivities (up to 95% ee). Moreover, virtually enantiopure 3-amino-1,2-diols could be obtained by the sequential combination of two reactions that both involve the use of a chiral catalyst.
authors.affiliation: Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637 (USA).
authors.forename: Chuan
authors.initials: C
authors.lastname: Wang
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry*; D002384:Catalysis; D014414:Tungsten / Q000737:chemistry*
chemical_list: D000605:Amino Alcohols; D014414:Tungsten
keywords: amino alcohols; kinetic resolution; regioselectivity; ring opening; tungsten