The asymmetric aminohydroxylation route to GABOB and homoserine derivatives
Michael Harding, Jennifer A Bodkin, Fatiah Issa, Craig A Hutton, Anthony C Willis, Malcolm D McLeod
TETRAHEDRON | PERGAMON-ELSEVIER SCIENCE LTD | Published : 2009
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.
Awarded by Australian Research Council
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.