The asymmetric aminohydroxylation route to GABOB and homoserine derivatives

M Harding; JA Bodkin; F Issa; CA Hutton; AC Willis; MD McLeod

Journal article

The asymmetric aminohydroxylation route to GABOB and homoserine derivatives

M Harding, JA Bodkin, F Issa, CA Hutton, AC Willis, MD McLeod

Tetrahedron | PERGAMON-ELSEVIER SCIENCE LTD | Published : 2009

DOI: 10.1016/j.tet.2008.11.037

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. © 2008 Elsevier Ltd. All rights reserved.

University of Melbourne Researchers

Craig Hutton Author

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Grants

Awarded by Australian Research Council

Funding Acknowledgements

Dr. Kelvin Picker, School of Chemistry, University of Sydney, is acknowledged for assistance with HPLC. We thank the Australian Research Council (DP0342590), the Australian National University and The University of Sydney for financial support.