Journal
TETRAHEDRON
Volume 65, Issue 26, Pages 5118-5124Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.03.012
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Funding
- NIH [R01-GM084022, GM08505, S10-RR04981-01]
- American Chemical Society
- NSF [CHE-9629688]
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We report an oxaziridine-mediated enantioselective aminohydroxylation of olefins catalyzed by a chiral copper(II) bis(oxazoline) complex. A variety of styrenic olefins undergo efficient aminohydroxylation with excellent regioselectivity and synthetically useful levels of enantioselectivity (up to 84% ee). The reaction can be conducted on multi-gram scale with as little as 2 mol % of the copper(II) catalyst. Hydrolysis of the resulting 1,3-oxazolines under acidic conditions produces N-sulfonyl amino alcohols that can be purified by recrystallization to afford very high levels of enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.
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