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The asymmetric aminohydroxylation route to GABOB and homoserine derivatives

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

Description

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.

CollectionsANU Research Publications
Date published: 2009
Type: Journal article
URI: http://hdl.handle.net/1885/53936
Source: Tetrahedron
DOI: 10.1016/j.tet.2008.11.037

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