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. 2014 Dec 8;53(50):13920-3.
doi: 10.1002/anie.201408732. Epub 2014 Oct 19.

Tungsten-catalyzed regio- and enantioselective aminolysis of trans-2,3-epoxy alcohols: an entry to virtually enantiopure amino alcohols

Chuan Wang  1 , Hisashi Yamamoto
Affiliations

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.

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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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