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The asymmetric aminohydroxylation route to GABOB and homoserine derivatives

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Date

2009

Authors

Harding, Michael
Bodkin, Jennifer A
Issa, Fatiah
Hutton, Craig A
Willis, Anthony
McLeod, Malcolm

Journal Title

Journal ISSN

Volume Title

Publisher

Elsevier

Abstract

The 4-nitrophenyl ether is an efficient directing group in the asymmetric aminohydroxylation reaction of homoallylic ether derivatives. Either regioisomeric product can be obtained with useful levels of enantioselectivity allowing for the short enantioselective synthesis of GABOB and homoserine derivatives. A model based on substrate-catalyst interactions is presented to explain the regio- and enantioselectivity of the aminohydroxylation reactions.

Description

Keywords

Keywords: 4 amino 3 hydroxybutyric acid; ether derivative; hydroxyamino acid; aminohydroxylation; article; catalyst; chemical interaction; chemical reaction; enantioselectivity; isomer; priority journal; synthesis Amino acid; Asymmetric aminohydroxylation; Asymmetric catalysis; Osmium; Regioselective

Citation

URI

http://hdl.handle.net/1885/53936

Collections

ANU Research Publications

Source

Tetrahedron

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1016/j.tet.2008.11.037

Restricted until

2037-12-31

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