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, 53 (50), 13920-3

Tungsten-catalyzed Regio- And Enantioselective Aminolysis of trans-2,3-epoxy Alcohols: An Entry to Virtually Enantiopure Amino Alcohols

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Tungsten-catalyzed Regio- And Enantioselective Aminolysis of trans-2,3-epoxy Alcohols: An Entry to Virtually Enantiopure Amino Alcohols

Chuan Wang et al. Angew Chem Int Ed Engl.

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.

Keywords: amino alcohols; kinetic resolution; regioselectivity; ring opening; tungsten.

Figures

Scheme 1
Scheme 1
Optimum reaction conditions for the asymmetric ring-opening of trans-2,3-epoxy cinnamyl alcohol with aniline as nucleophile.
Scheme 2
Scheme 2
Investigation of the Ligand-effect on the Outcome of the Ring-opening Reaction.
Scheme 3
Scheme 3
Derivatization of the ring-opening products to biologically active compounds in optically pure form.

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