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Org Lett. 2003 Feb 6;5(3):281-4.

The use of pH to influence regio- and chemoselectivity in the asymmetric aminohydroxylation of styrenes.

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1
Department of Chemistry, Roger Adams Laboratory, University of Illinois, Urbana, Illinois 61801, USA.

Abstract

[reaction: see text] The pH-controlled Sharpless asymmetric aminohydroxylation (AA) of styrenes provides 1-aryl-2-amino ethanols (regioisomer B) with high enantio-, chemo-, and regioselectivity. As existing AA protocols typically give regioisomer A as the major reaction product when using carbamate nitrogen sources, this method is a convenient alternative for the selective production of regioisomer B.

PMID:
12556172
DOI:
10.1021/ol027242j
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