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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.

SUBMITTER: Wang C

PROVIDER: S-EPMC4293429 | biostudies-literature | 2014 Dec

REPOSITORIES: biostudies-literature

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

Wang Chuan C Yamamoto Hisashi H

Angewandte Chemie (International ed. in English) 20141019 50

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. ...[more]

PMID: 25328028

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