Journal
TETRAHEDRON
Volume 65, Issue 4, Pages 831-843Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.11.037
Keywords
Asymmetric aminohydroxylation; Amino acid; Osmium; Asymmetric catalysis; Regioselective
Categories
Funding
- Australian Research Council [DP0342590]
- The University of Sydney
- Australian Research Council [DP0342590] Funding Source: Australian Research Council
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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. (C) 2008 Elsevier Ltd. All rights reserved.
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